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

HRID 1789009Notes

Reaction equation

HRID 1789009 reaction equation
[CH3:1][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]>>[F:13][CH2:14][C:15]1[NH:22][C:23]([CH3:31])=[C:24]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[CH3:1])[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 3

HCID 2622412-Methyl-3-nitrobenzaldehydeHCID 3271821Isopropyl3-aminocrotonateHCID 14170515Methyl 4-fluoro-3-oxobutanoate

Product 1

HCID 700912543-Methyl 5-(1-methylethyl) 2-(fluoromethyl)-1,4-dihydro-6-methyl-4-(2-methyl-3-nitrophenyl)-3,5-pyridinedicarboxylateYield 20%

Procedure

2-Methyl-3-nitrobenzaldehyde (1.23 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.07 g, 7.5 mmoles) were heated with stirring at 80° for 2.5 hours. The cooled residue was chromatographed twice on silica eluting first with ethyl acetate/petroleum ether (60°-80°) and then with ethyl acetate/methylene chloride. The title compound (0.61 g) was obtained by crystallisation from a mixture of petroleum ether (60°-80°) and 2-propanol mp 132°-133°.

Workup

  1. customThe cooled residue was chromatographed twice on silica eluting first with ethyl acetate/petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-4827bcb196ef443d97806bbf4f85f6ef
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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