Methanol → Nifedipine

HRID 358391Notes

Reaction equation

HRID 358391 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH3:12][C:13]([CH2:15][C:16]([OH:18])=[O:17])=O.[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[NH4+:27].[OH-].N1C=CC=CC=1.[CH3:35]O>>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]1[C:15]([C:16]([O:18][CH3:35])=[O:17])=[C:13]([CH3:12])[NH:27][C:21]([CH3:23])=[C:20]1[C:19]([O:25][CH3:26])=[O:24])([O-:3])=[O:2]

Participants

6

Reactant 5

HCID 887MethanolHCID 1049PyridineHCID 7757Methyl acetoacetateHCID 14923Ammonium HydroxideHCID 131713665HCID 131713665, compound

Product 1

HCID 4485Nifedipine

Conditions

Temperature
15 °C

Procedure

2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.2 mole, 23.2 g) and NH4OH (12 ml) were heated in methanol (20 ml) in the presence of pyridine for several (7) hours. After cooling to 15° C. the precipitated product was filtered off. The crude product was crystallized from acetic acid to yield 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (21.7 g, 62% of the theory), m.p. 172°-174° C.

Workup

  1. filtrationwas filtered off
  2. customThe crude product was crystallized from acetic acid

Sources & evidence

ORD record
ord-b1d9957efac4496f95ba8a0c9c1ff410
Source dataset
uspto-grants-1984_08
Patent number
US04467093

Reaction notes

Loading…