Isopropyl3-aminocrotonate → 3-Methyl 5-(1-methylethyl) 4-(2-chloro-3-nitrophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789012Notes

Reaction equation

[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:13][CH2:14][C:15](=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18].[NH2:22][C:23]([CH3:31])=[CH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>>[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:24]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[C:23]([CH3:31])[NH:22][C:15]([CH2:14][F:13])=[C:16]1[C:17]([O:19][CH3:20])=[O:18]

Participants

Reactant 3

HCID 3271821Isopropyl3-aminocrotonate

HCID 126677132-Chloro-3-nitrobenzaldehyde

HCID 14170515Methyl 4-fluoro-3-oxobutanoate

Product 1

HCID 700911963-Methyl 5-(1-methylethyl) 4-(2-chloro-3-nitrophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateYield 42.2%

Procedure

2-Chloro-3-nitrobenzaldehyde (1.38 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.06 g, 7.5 mmoles) were heated at 90° for 2.5 hours. The reaction mixture was chromatographed on silica eluting with petroleum ether (60°-80°)/ethyl acetate mixtures. The title compound (1.35 g) was obtained after crystallisation from petroleum ether (60°-80°)/2-propanol. mp 156°-7°.

Workup

customThe reaction mixture was chromatographed on silica eluting with petroleum ether (60°-80°)/ethyl acetate mixtures

Sources & evidence

ORD record: ord-3f985ae4fcda40fb9f350a1c1e8e47d8
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04686217

Reaction notes

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