Acetic Acid → Methyl 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-phenylpyridine-3-carboxylate

HRID 414230Notes

Reaction equation

HRID 414230 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:10]([CH3:11])[NH:19][C:20]([CH3:26])=[C:21]2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 643918Methyl 3-aminocrotonate2×HCID 537140661-(3-Chlorophenyl)-2-phenyl-3-oxo-1-butene

Product 1

HCID 13670890Methyl 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-phenylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.82 g (50 mmol) of 1-(3-chlorophenyl)-2-phenyl-3-oxo-1-butene in 80 ml of ethanol are heated to reflux with 11.5 g (100 mmol) of methyl β-aminocrotonate and 6 ml (100 mmol) of acetic acid overnight. 11.5 g of methyl β-aminocrotonate and 6 ml of acetic acid are added once more, and the mixture is heated under reflux for 24 hours. On cooling, crystals are produced, and these are filtered off with suction and washed with ethanol. For complete purification, they are passed through a silica gel column using toluene/ethyl acetate 20:1. 5.3 g of a colorless substance, of melting point 191° C., are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 24 hours
  3. temperatureOn cooling
  4. customcrystals are produced
  5. filtrationthese are filtered off with suction
  6. washwashed with ethanol
  7. customFor complete purification, they
  8. custom5.3 g of a colorless substance, of melting point 191° C., are obtained

Sources & evidence

ORD record
ord-ff60772eb23a4e5594f571a789c1dadc
Source dataset
uspto-grants-1988_12
Patent number
US04791122

Reaction notes

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