Metoprolol tartrate
Molecular Weight (MW)
684.81 | |
Formula | 2C15H25NO3.C4H6O6 |
CAS No. | 56392-17-7 |
http://repository.ias.ac.in/11453/1/11453.pdf
2-Chloro-1-(4-hydroxyphenyI)ethanone (2) separated out and was filtered. The solid was crystallized from methanol. Yield 8.52 g (50%), rn.p. 151" (lit. 5m.p.151-152").1R:(KBr)1655crn-l.
'H NMR (CDC13) : 6 4.58 (s, 2H); 6.8 (d, 2H, J = 9 Hz); 7.72 (d, 2H, J = 9 Hz). MS : Mi 120.5.
2-methoxy-l-(4-hydroxyphenyl)ethanone (3) (2.98 g, 90%) as white solid. m.p. 133-135". IR : (KBr) 3300, 1660 cm-l. 'H NMR (CDC13) : 6 3.4 (s, 3H); 4.55 (s, 2H); 6.8 (d, ZH, J = 9 Hz); 7.75 (d, 2H, J = 9 Hz); 9.6 (bs, lH, -OH). MS : M+ 166. Analysis calculated for CqHI0O3 : C, 65.05; H, 6.07. Found : C, 64.88; H, 6.27%.
4-( 2-Me thoxyethy1)phenol (4) A solution of 3 (1.66 g, 10.0 rnmol) and 10% paliadium-char- coal (86 mg) in ethanol (40 ml) was hydrogenated at 45 psi for 4 h. The solution was filtered, washed with ethanol and concen- trated to afford the crude product which was distilled (b.p. 125O/ 3 mm) to afford pure 4 (1.46 g, 96%). IR : (film) 3300. 'H NMR (CDC13) : 6 2.84 (t, 2H, 3 = 7 Hz); 3.42 (s, 3H); 3.65 (t, 2H, J = 7 Hz); 6.74 (d, 2H, J = 9 Hz); 7.1 (d, ZH, J = 9 Hz); 7.0 (br, 1H). MS: Mf 152.
4-(2-Methoxyethyl)phenoxyallyl ether (5) A rnixture of 4 (1.52 g, 10.0 mmol), potassium carbonate (1.52 g, 11.0 mmol) and ally1 bromide (1.33 g, 11.0 mrnol) in acetone (25 ml) was refluxed for 7 h. The reaction mixture fiitered. Acetone was removed under reduced pressure. The residue so obtained was dissolved in ethyl acetate. The ethyl acetate layer was washed . with IN NaOH solution, water, dried (Na2S04) and concentrated to afford 5 (1.63 g, 85%) a\ colourless liquid. 'H NMK (CDCI3) : 6 2-81 (t, 2H, 3 = 7 Hz); 3.36 (5, 3H); 3.60 (t, 2H, J = 7 Hz); 4.5 (d, 2H); 5.10-5.54 (rn, 2H); 5.77-6.32 (m, IH); 6.83 (d, 2H, 3 = 9 Hz); 7.13 (d, 2H, J = 9 Hz). MS : M+ 192.
3[4-(2-Methoxyethy1)phenoxyl-1,Z-propanediol(6)
6 as d syrapy liquid (1.26 g, 80%). IK (nujol) : 3300 c in . H NMK (CDC'13) -1 1 : 6 2.8 (t, 2H, 3 = 7 Hz); 3.3 (s, 3H); 3.55 (t, 2H, J = 7 Hz); 3.62- 4.44 (rn, 5H); 6.81 (d, 2H, J = 9 Hz); 7.1 (d, 2H, J 9 H7). 1Vl5 : M' 226.
3-[4-(2-Methoxyethyl)phenoxyl-l,2-epoxypropane(7)
7 (0.50 g) as a gurrirny liquid. 'H NMK (CDCl,) : 6 2.74-3.00 (m, 4H); 3.42 (5, 3H); 3.62 (rri, 3H); 3.87-4.04 (111, 2H); 6.9 (d, 2H, 3 9 Hz); 7.2 (d, 2H, J = 9 Hz).
SPECTRAL DATA
4-(2-Methoxyethyl)phenoxyallyl ether (5) A rnixture of 4 (1.52 g, 10.0 mmol), potassium carbonate (1.52 g, 11.0 mmol) and ally1 bromide (1.33 g, 11.0 mrnol) in acetone (25 ml) was refluxed for 7 h. The reaction mixture fiitered. Acetone was removed under reduced pressure. The residue so obtained was dissolved in ethyl acetate. The ethyl acetate layer was washed . with IN NaOH solution, water, dried (Na2S04) and concentrated to afford 5 (1.63 g, 85%) a\ colourless liquid. 'H NMK (CDCI3) : 6 2-81 (t, 2H, 3 = 7 Hz); 3.36 (5, 3H); 3.60 (t, 2H, J = 7 Hz); 4.5 (d, 2H); 5.10-5.54 (rn, 2H); 5.77-6.32 (m, IH); 6.83 (d, 2H, 3 = 9 Hz); 7.13 (d, 2H, J = 9 Hz). MS : M+ 192.
3[4-(2-Methoxyethy1)phenoxyl-1,Z-propanediol(6)
6 as d syrapy liquid (1.26 g, 80%). IK (nujol) : 3300 c in . H NMK (CDC'13) -1 1 : 6 2.8 (t, 2H, 3 = 7 Hz); 3.3 (s, 3H); 3.55 (t, 2H, J = 7 Hz); 3.62- 4.44 (rn, 5H); 6.81 (d, 2H, J = 9 Hz); 7.1 (d, 2H, J 9 H7). 1Vl5 : M' 226.
3-[4-(2-Methoxyethyl)phenoxyl-l,2-epoxypropane(7)
7 (0.50 g) as a gurrirny liquid. 'H NMK (CDCl,) : 6 2.74-3.00 (m, 4H); 3.42 (5, 3H); 3.62 (rri, 3H); 3.87-4.04 (111, 2H); 6.9 (d, 2H, 3 9 Hz); 7.2 (d, 2H, J = 9 Hz).
SPECTRAL DATA
Metoprolol tartrateIR
The 1H Metoprolol tartrate
The 13C NMR spectra Metoprolol tartrate
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MOM WILL TEACH YOU NMR
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