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

HRID 621540Notes

Reaction equation

HRID 621540 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:21]([C:24]1[CH:25]=[C:26]([CH:39]=[CH:40][CH:41]=1)[CH:27]=[C:28]([C:36]([CH3:38])=O)[C:29]([O:31][CH2:32][CH:33]1[CH2:35][CH2:34]1)=[O:30])([O-:23])=[O:22].[NH3:42]>C(O)C>[CH3:38][C:36]1[NH:42][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH3:11])=[O:6])[CH:27]([C:26]2[CH:39]=[CH:40][CH:41]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:28]=1[C:29]([O:31][CH2:32][CH:33]1[CH2:35][CH2:34]1)=[O:30]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 99937542-[N-(4-methoxybenzyl)-N-methylamino]-ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Product 1

HCID 141000943-cyclopropylmethyl 5-[2-[N-(4-methoxybenzyl)-N-methylamino]ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.8 g (30 mmol) of 2-[N-(4-methoxybenzyl)-N-methylamino]-ethyl acetoacetate, 8.5 g (30 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 2.5 ml of 28% aqueous ammonia and 50 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 to afford 3-cyclopropylmethyl 5-[2-[N-(4-methoxybenzyl)-N-methylamino]ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (7.8 g, 46.7%) as yellow oil. Treatment of this oil with 1 equivalent of fumaric acid in ethanol gave the corresponding fumarate.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-421a5e6b1cbb46c884b4372d8c7a8390
Source dataset
uspto-grants-1989_04
Patent number
US04824855

Reaction notes

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