Methyl acetoacetate → Nifedipine

HRID 893795Notes

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].[OH-:12].[NH4+:13].[C:14]([O:20][CH3:21])(=[O:19])[CH2:15][C:16]([CH3:18])=O>>[CH3:18][C:16]1[NH:13][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH3:21])=[O:19])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:15]=1[C:14]([O:20][CH3:21])=[O:12]

Participants

Reactant 3

HCID 7757Methyl acetoacetate

HCID 111012-Nitrobenzaldehyde

HCID 14923Ammonium Hydroxide

Product 1

HCID 4485NifedipineYield 81%

Procedure

One proceeds as described in Example 7 except that 0.4 mole of 2-nitro-benzaldehyde, 0.415 mole of a 25% aqueous ammonium hydroxide solution and 1.40 moles of methyl acetoacetate are used. Thus 112.1 g of nifedipine are obtained, yield 81%, m.p.: 172°-175° C. The product complies with the requirements of USP XXI without further purification.

Sources & evidence

ORD record: ord-6916f565fb9948ff8ce2084ff9af461f
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05126457

Reaction notes

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