2-Butenoic acid, 3-amino-, ethyl ester → Ethyl 2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate

HRID 358588

Reaction equation

HRID 358588 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]([CH3:19])=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C.N1CCCCC1>[CH3:19][C:12]1[NH:11][CH:9]=[CH:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 953082-Butenoic acid, 3-amino-, ethyl esterHCID 637511Cinnamaldehyde

Product 1

HCID 14652661Ethyl 2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylateYield 72.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8082PiperidineSolvent

Procedure

(E)-3-Phenyl-2-propenal (13.8 ml, 0.11 mol) and ethyl 3-amino-2-butenoate (12.9 g, 0.1 mol) were dissolved in 150 ml of absolute ethanol containing 0.5 ml of piperidine. The mixture was heated under reflux for 18 hours followed by removal of the solvent under vacuum to yield 17.6 g of ethyl 1,4-dihydro-2-methyl-4-phenyl-3-pyridinecarboxylate as a brown viscous oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customfollowed by removal of the solvent under vacuum

Sources & evidence

ORD record
ord-42e9defa45784b289909b967b73d63bc
Source dataset
uspto-grants-1991_03
Patent number
US04997837

Linked notes

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