N CHLORO ISATIN

http://www.scielo.br/scielo.php?pid=S0103-50532011000200010&script=sci_arttext

Journal of the Brazilian Chemical Society

Print version ISSN 0103-5053

J. Braz. Chem. Soc. vol.22 no.2 São Paulo Feb. 2011

http://dx.doi.org/10.1590/S0103-50532011000200010 

Spectroscopic data

1a: IR (film) ν _max/cm^-1: 3085, 2923, 1764, 1729, 1614, 1596, 1483, 1315, 1294, 1176, 1126, 950, 427. 

¹H NMRδ (200 MHz, CDCl₃): 3.23 (3H, s), 6.85 (1H, d, J 8.0 Hz), 7.51-7.57 (2H, m); 

¹³C NMR δ (50 MHz, CDCl₃): 26.5 (CH₃), 111.4 (CH), 118.3 (q), 125.2 (CH), 129.7 (q), 137.9 (CH), 149.8 (q), 157.8 (q), 182.4 (q); 

MS (70 eV)m/z 195 [M] ⁺, 197 [M+2] ⁺, 160, 104.

Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum

figure 3 1H NMR spectrum of 5-hydroxy-7-methoxy-4-methylphthalide (400 MHz, DMSO). 

The ¹H NMR spectrum of 5-hydroxy-7-methoxy-4-methylphthalide (Figure 3) showed signals for methyl group at δ 1.95 (H-9, singlet, 3H), a signal for the methoxyl group at δ 3.79 (H-8, singlet, 3H), a signal corresponding to one methylene group at δ 5.15 (H-3, singlet, 2H), and a signal for aromatic hydrogen at δ 6.49 (H-6, singlet, 1H).

Figure 1 Structures of the compounds mycophenolic acid and 5-hydroxy-7-methoxy-4-methylphthalide. 

TABLE I 1H, 13C and gHMBC NMR data for the compounds mycophenolic acid and 5-hydroxy-7methoxy-4methylphthalide 

Position		Mycophenolic acid		5-hydroxy-7methoxy-4methylphthalide
	δ 13C	δ 1H(multiplicity, J in Hz)	1H-13C gHMBC*	δ 13C	δ 1H(multiplicity, J in Hz)	1H-13C gHMBC *
1	173.0	-		173.0	-	-
3	70.0	5.18 (2H, br s)	1; 3a	68.0	5.15 (2H, br s)	1; 3a; 4; 5; 7; 7a
3a	122.1	-	-	104.0	-	-
4	116.7	-	-	110.0	-	-
5	163.7	-	-	163.0	-	-
6	106.4	-	-	98.0	6.49 (1H, s)	1; 4; 5; 7; 7a
7	153.7	-	-	158.0	-	-
7a	144.0	-	-	151.0	-	-
8	61.0	3.74 (3H, s)	5	57.0	3.79 (3H, s)	7
9	11.5	2.13 (3H, s)	3; 3a; 4; 5	11.0	1.95 (3H, s)	3a; 4; 5
OH	-	7.67 (1H, br s)	-	-	10.59 (1H, br s)	4; 6; 5
1’	179.1	-	-	-	-	-
2’	32.7	2.38-2.47 (2H,m)	1’; 3’; 4’	-	-	-
3’	34.2	2.24-2.32 (2H,m)	1’; 2’; 4’; 5’; 7’	-	-	-
4’	133.9	-	-	-	-	-
5’	123.0	5.23-5.28 (1H,m)	3’; 7’	-	-	-
6’	22.3	3.37 (2H, br d; 6.8)	5; 7; 5’	-	-	-
7’	16.1	1.78 (3H, s)	3’; 4’; 5’		-	-

Abbreviations: s - singlet, br s - broad singlet, br d - broad doublet, m - multiplet.

Figure 2 1H NMR spectrum of mycophenolic acid (400 MHz, CDCl₃). 

The ¹H NMR spectrum of the mycophenolic acid (Figure 2) showed signals for a methyl group at δ 1.78 (H-7', singlet, 3H) and a methyl group linked to aromatic ring at δ 2.13 (H-9, singlet, 3H), a signal for a methoxyl group at δ 3.74 (H-8, singlet, 3H), two signals corresponding to aliphatic methylenes in the region of δ 2.47 to δ 2.38 (H-3a' and H-3b', multiplet 2H), of δ 2.32 to δ 2.24 (H-2', multiplet, 2H), a broad doublet for a methylene group at δ 3.37 (H-6', 2H), a broad singlet at δ 5.18 (H-3, 2H) referring to an aliphatic methylene bearing oxygen, and a multiplet for a methyne group of δ 5.23 to δ 5.28 (H-5',1H).

Figure 4 gHMBC NMR experiment of 5-hydroxy-7-methoxy-4-methylphthalide (400 MHz, DMSO) and important long range correlations detected. 

Anais da Academia Brasileira de Ciências

Print version ISSN 0001-3765

An. Acad. Bras. Ciênc. vol.85 no.2 Rio de Janeiro Apr./June 2013 Epub June 17, 2013

http://dx.doi.org/10.1590/S0001-37652013005000024 

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Synthesis of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole.

Synthesis of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole.

To 1.5 g (0.00739 mol) of 3,4,5-trinitro-1H-pyrazole in 20 ml of diethyl ether at 0 ° C was added dropwise a solution of 1 g (0.00739 mol) of 1,3-svezhevozognannogo dehydroadamantane in 20 ml of diethyl ether. The mixture was kept under stirring for 1 hour at 0 ° C, the temperature was raised why to reflux and held for an additional 3 hours. The solvent was distilled off. The product was purified by recrystallization from ethanol.

Yield 2.44 g (98%). Mp = 139-140 ° C.

Mass spectrum, m / z (intensity,%): 337 (M ⁺ , 2%), 292 ([M-NO ₂ ] ⁺ , 2%), 247 (2%), 245 ([M- (NO ₂ ) ₂ ] +, 2%), 199 ([M-3NO ₂ ] ⁺ , 2%), 177 (36%), 151 (21%), 150 (48%), 135 (Ad ⁺ , 96%), 121 (48%), 107 (56%) 95 (71%), 93 (100%) 67 (45%) 55 (75%).

NMR ¹ H (300 MHz, DMSO-d ₆ ), δ, ppm .: 1.66 (6H, CH ₂ , H _delta -Ad), with 2.1 (3H, CH, H _y -Ad), 2.18 to (6H, CH ₂ , H _beta -Ad).

NMR ¹³ C (75.47 MHz, CDCl ₃ ), δ, ppm .: 71.8872 (s, 1C, C _alpha -Ad), 41.0302 (s, 3C, C _beta -Ad), 35.2616 (s, 3C, C _delta -Ad), 29.9234 (s, 3C, C _y -Ad).

A process for production of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole (RU 2528404):

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