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

HRID 1789008Notes

Reaction equation

HRID 1789008 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:11][CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16].[NH2:20][C:21]([CH3:29])=[CH:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:22]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[C:21]([CH3:29])[NH:20][C:13]([CH2:12][F:11])=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 3271821Isopropyl3-aminocrotonateHCID 14170515Methyl 4-fluoro-3-oxobutanoate

Product 1

HCID 197964883-(Methyl) 5-(1-methylethyl) 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateYield 38.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,3-Dichlorobenzaldehyde (1.75 g, 10 mmoles), methyl 4-fluoro-3-oxobutanoate (1.34 g, 10 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.43 g, 10 mmoles) were heated with stirring at 90° for 2.5 hours. The reaction mixture was dissolved in ethyl acetate and chromatographed on silica eluting with petroleum ether (60°-80°)/ethyl acetate mixtures. Pure fractions were combined and evaporated to dryness. The title compound (1.6 g) was obtained by crystallisation from 2-propanol. mp 148°-9°.

Workup

  1. customchromatographed on silica eluting with petroleum ether (60°-80°)/ethyl acetate mixtures
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-89d964b5325847acaadeeabb191fdf1c
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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