Ammonia → 3-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 621538Notes

Reaction equation

HRID 621538 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:13]([C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[CH:19]=[C:20]([C:28]([CH3:30])=O)[C:21]([O:23][CH2:24][CH:25]1[CH2:27][CH2:26]1)=[O:22])([O-:15])=[O:14].[NH3:34]>C(O)C>[CH3:30][C:28]1[NH:34][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])=[O:6])[CH:19]([C:18]2[CH:31]=[CH:32][CH:33]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)[C:20]=1[C:21]([O:23][CH2:24][CH:25]1[CH2:27][CH2:26]1)=[O:22]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 125291702-(Dimethylamino)ethyl 3-oxobutanoateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Product 1

HCID 141000923-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.0 g (75 mmol) of 2-(N,N-dimethylamino)ethyl acetoacetate, 21.7 g (75 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)-acetoacetate, 6.0 ml of 28% aqueous ammonia and 70 ml of ethanol was stirred at the reflux temperature for 7 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column and crystallized from ethyl ether to afford 3-cyclopropylmethyl 5-[2-(N,N-dimethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (14.1 g, 42.3%) as yellow crystals.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column
  3. customcrystallized from ethyl ether

Sources & evidence

ORD record
ord-d1d330aa5135410dae686dc7f283cdd0
Source dataset
uspto-grants-1989_04
Patent number
US04824855

Reaction notes

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