3-Chlorobenzaldehyde → 5-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 890162Notes

Reaction equation

HRID 890162 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]#[N:9])(=[O:4])[C:2]#[CH:3].[C:10]([O:14][CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:13])[C:11]#[CH:12].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O.C([O-])(=O)C.[NH4+:37]>C(O)(=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]2[C:11]([C:10]([O:14][CH2:15][CH:16]=[CH:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:13])=[CH:12][NH:37][CH:3]=[C:2]2[C:1]([O:5][CH2:6][CH2:7][C:8]#[N:9])=[O:4])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 204932242-Cyanoethyl prop-2-ynoateHCID 53746771(3-Phenyl-2-propene-1-yl) propiolate

Product 1

HCID 695898685-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

493 mg (4.0 mmol) of (2-cyanoethyl) propiolate, 745 ml (4.0 mmol) of (3-phenyl-2-propene-1-yl) propiolate, 0.453 ml (4.0 mmol) of 3-chlorobenzaldehyde and 617 mg (8.0 mmol) of ammonium acetate were heated at 60° C. under stirring in 8 ml of acetic acid for 12 hours. Acetic acid was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound.

Workup

  1. customAcetic acid was evaporated under reduced pressure
  2. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-28dfbe147392458b8579f387dea07187
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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