2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine

¹H-NMR (200 MHz; CDCl₃): δ 8.30 (d, J = 8.8 Hz, 2H), 8.23 (s, 1H), 7.93-7.88 (m, 2H), 6.86-6.77 (m, 3H), 3.95 (td, J = 7.1, 1.1 Hz, 2H), 3.87 (d, J = 7.7 Hz, 6H), 3.03 (t, J = 7.1 Hz, 2H).

Procedure
4-Nitrobenzaldehyde (4.6 g, 30.4 mmol, 1 eq) was suspended in diethyl ether (40 mL). 3,4-dimethoxyphenethylamine (5 mL, 30.3 mmol, 1 eq) was added, dropwise, to the stirring mixture, after which the solution went a clear dark orange colour. The reaction mixture was left to stir at rt from 13:30.
At 4:30 (+3 hours), a fine yellow precipitate had formed and in the now colourless solution. The solvent was removed under reduced pressure to give crude KAB23-1 as a fine yellow powder (10.0 g, 105%).
Purification
27/03/12. A test recrystallisation from hot ethanol was performed according to the literature.^[1]Start: 779 mg. ReXST: 610 mg. Yield: 78%.
Fine yellow needles were formed. The crystals were filtered and washed with EtOH, then dried under a high vacuum.
The remainder of the sample was recrystallised from hot EtOH. The flask was left to stand at rt overnight before the crystals were filtered, then washed with EtOH and dried under a high vacuum for 6 hours. Start: 9.1 g. reXST: 7.9 g. Yield 87%.


References
[1] R. Gitto, M. L. Barreca, L. De Luca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, A. Chimirri, Journal of Medicinal Chemistry 2003, 46, 197.

1-(3,4-dimethoxyphenyl)ethanol

1-(3,4-dimethoxyphenyl)ethanol
Geza Arvai,

http://www.google.com/patents/WO1999006343A1?cl=en

Example 1.

Into a 10-L hydrogenation vessel, equipped with an internal coil for heating and cooling, stirrer, manometer and thermometer, 3.5 kg (19,4 mol) of 3,4-dimethoxy- acetophenone are placed and to it 0.26 kg (0,074 mass part) slurry of finely- powdered Raney-nickel (pH=8-9) promoted catalyst are washed with 1 kg of water. The reactor is filled with 3.5 kg of water, flushed with nitrogen, then with hydrogen, and under intensive stirring (revolution per minute is approx. 1420 min^"1) the mixture is reacted at 70-85°C with hydrogen under 8-10 bar. After 7 hours the hydrogen consumption is ceased. Closing the hydrogen inlet, the reaction is post- hydrogenated for half an hour, then it is cooled. The catalyst is removed by filtration. The filtrate is concentrated in vacuo (20 torr) by a rotary evaporator, in a 40-50°C water-bath. The product is a yellow viscous oil, weight 3.48 kg (19, 1 mol, 98,5%). Refractive index (Na_D, 25°C) is 1,5385; assay by HPLC is 97,3%; water content by Karl-Fisher method is 1,2%. TLC (Kieselgel 60 F₂₅ benzene-EtAc 7:3 v/v) shows one spot (Rf=0.28, visualized by UV light and PMA).

An aliquot part is crystallized from 1.5-fold volume of diethyl ether - light petroleum (2:1, v/v) mixture. Melting point of the thus obtained white crystals is 34- 35 °C.

Confirmation of structure

IR (KBr, cm"¹) v: 3312, 3056, 3006, 2966, 2926, 2880, 2844, 1608, 1594, 1522, 1467, 1261, 1237, 1162, 1140, 1091, 1075, 1028, 861, 814.

 IH-NMR (200 MHz, CDC1₃) δ: 1.47 (3H, d, J=6.4 Hz, CH₃), 2.08 (IH, s, OH),

3.86 and 3.88 (total 6H, each s, CH₃0), 4.83 (IH, q, J=6.4 Hz, CHOH), 6.79-6.93 (3H, m, aromatic).

¹ C-NMR (50 MHz, CDCI3) δ: 25.05 (CH₃), 55.79 and 55.89 (CH₃0), 70.10

(ArCH), 108.65 (C-2), 1 10.98 (C-5), 1 17.48 (C-6), 138.57 (C-l), 148.28 and 149.0 (C-3, C-4).



Literature data

CAS No: 5653-65-6

CA name: l-(3,4-dimethoxyphenyl)-ethanol B.p. 145-150 (4 torr), refractive index (Zhur. Obshchei Khim. 27, 2142 (1957), CA 52; 8089g) (Na_D 20°C) 1.5440.

• IH-NMR (200 MHz, CDC1₃) δ: 1.48 (d, J=6.5 Hz), 3.86 and .89 (s), 4.84 (q), 6.8-6.94 (m).

• 13c-NMR (^Ann- ¹⁹⁷⁷- ⁵⁸⁸) (^{50 MHz}' ^CDC13) δ: 25.0, 55.8, 55.9, 70.1, 108.7, 111.1, 117.5, 138.6, 148.4, 149.1.

Geza Arvai

process chemist at Sanofi

Hungary area

Pharmaceuticals

hu.linkedin.com/pub/geza-arvai/23/90a/165

• chemwiz@freemail.hu
• http://www.sanofi.hu/l/hu/hu/index.jsp

Üdvözöljük a Sanofi

magyarországi oldalán

Process for the preparation of 1-(3,4-dimethoxyphenyl)-ethanol(Link)

Europe WO9906343

Issued July 31, 1997

The subject of our invention is the process for the preparation of the 1-(3,4-dimethoxypheny)ethanol of formula (I), by the reduction of 3,4-dimethoxyacetophenone of formula (II), characterized in that the carbonyl group of the 3,4-dimethoxyacetophenone of formula (II) is reduced by 1 mol of hydrogen under the conditions of catalytic hydrogenation.

(Open)6 inventors, including:

• 

  Geza Arvai

  process chemist at Sanofi

• 

  Béla Bertók

  Project Supervisor at Cominnex Co Ltd.

• 

  Aradi Mátyás

• 

  Szalay Erzsébet

.........
sanofi budapest

Colorless, Mp: 103 °C;

Molecular formula C16H20N4;

1H-NMR (250 MHz, CDCl3):
(ppm) 0.99 (s, 6H, CH3), 2.69 (br, 4H, CH2), 3.24 (br, 2H, NH), 7.10–8.20 (3m, 10H, Py–H),

13C-NMR
(62.5 MHz, CDCl3): (ppm) 24.83 (2CH3), 28.29 (C), 53.43 (2CH2), 75.82 (CN2) 122.09, 122.15 (p-CH
and m-CH), 136.70 (o-CH), 149.04 (m-CHN), 162.23 (i-C-Py).

Calcd. for C16H20N4: C, 71.61; H, 7.51;
N, 20.88. Found: C, 71.25; H, 7.31; N, 20.55).

[M+] = 270 m/z.

IR: 3390 cm−1N-H, 3080 cm−1C–H Py,2980–2700 cm−1C-H aliphatic.

Molbank 2015, 2015(1), M838; doi:10.3390/M838

Short Note

5,5-Dimethyl-2,2-di(pyridin-2-yl)hexahydropyrimidine

Ahmad. Abu-Obaid ¹, Ahmad I. Asadi ¹, Afaf. Alruwaili ², Heba. Atieh ¹, Shoqour Khlaif ¹, Taibi Ben Hadda ³, Smaail Radi ³, Belkheir Hammouti ⁴ andIsmail Warad ^1,*

Dr Ismail warad

warad@najah.edu

- Authors' affiliations

¹ Department of Chemistry, AN-Najah National University P.O. Box 7, Nablus, Palestine

² Department of Chemistry, College of Science, University of Hail, P.O. Box 2440, Hail, Saudi Arabia

³ Laboratoire LCM, Faculty of Science, University Mohammed Premier, Oujda-60000, Morocco

⁴ LCAE-URAC18, Faculty of Science, University Mohammed Premier, Oujda-60000, Morocco

Abstract: Novel 5,5-dimethyl-2,2-di(pyridin-2-yl)hexahydropyrimidine was synthesized in good yield by a one-pot condensation reaction of 2,2-dimethylpropane-1,3-diamine with di(pyridin-2-yl)methanoneusing dichloromethane as solvent at room temperature. The structure of the synthesized compound was assigned on the basis of its elemental analysis, UV-visible, 1H-NMR, 13C-NMR, IR, and mass spectral data.

http://www.mdpi.com/1422-8599/2015/1/M838



An-Najah National University is a vibrant hub of learning which nourishes science, knowledge and understanding. An-Najah offers undergraduate instruction in ...







Dr. Iz-Addin noted that the idea of the Bioequivalence Unit began in 1994 with the establishment of the Faculty of Pharmacy. Since that time, An-Najah has made considerable progress in the field of pharmacy, conducting a number of studies throughout the 1990s and founding The Drug Control and Biological and Chemical Analysis Center in 1999. Since its establishment, the Center has been working in cooperation with the Ministry of Health to offer drug analysis services. In order to build on its pharmaceutical research and services, the University launched a feasibility study in 2009, examining the possibility of founding a bioequivalence unit. Following the results of the study, in 2012, the University presented a formal application to the Ministry of Health to receive the first accreditation for a unit focusing on bioequivalence studies. 

Nablus palestine











PALESTINE

trans-Chalcone

 

trans-Chalcone

IR




MASS



RAMAN



 13 C NMR

 






1H NMR









DEPT 90
 

 HSQC
 


 HMBC
 



COSY
 



TOCSY







 Chemistry Letters, 24, p. 987, 1995
Journal of the American Chemical Society, 104, p. 4724, 1982
Tetrahedron Letters, 8, p. 1861, 1967

[4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-yl]methanol

Reference Example 44[4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-yl]methanol
• 
• In the same manner as in Reference Example 6, the title compound was obtained as a colorless oil from 4'-(benzyloxy)-2',6'-dimethyl-3-biphenylcarbaldehyde. yield 95%.
  
  ¹H NMR (CDCl₃) δ: 1. 65 (1H, t, J=5.9Hz), 2.01 (6H, s), 4. 73 (2H, d, J=5.9Hz), 5. 07 (2H, s), 6. 75 (2H, s), 7. 07 (1H, d, J=7.3Hz), 7.13 (1H, s), 7. 30-7.48 (7H, m).
   http://www.google.com/patents/EP1630152A1?cl=en
  
  
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