Methanol → Nifedipine

HRID 358392Notes

Reaction equation

HRID 358392 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-].[CH3:29]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][CH3:29])=[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

5

Reactant 4

HCID 887MethanolHCID 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 (0.21 mole, 26 g), NH4OH (12 ml) and methanol (45 ml) were heated under reflux for 5 hours. After cooling to 15° C. the precipitated product was filtered off. The crystallization of the crude product from acetic acid yielded 4-(2'-nitrophenyl)-2,6 dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (19.0 g, 55% of the theory), m.p. 173°-174° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationwas filtered off
  3. customThe crystallization of the crude product from acetic acid

Sources & evidence

ORD record
ord-cd45dff0420743c8985e0405aedb09ff
Source dataset
uspto-grants-1984_08
Patent number
US04467093

Reaction notes

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