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

HRID 621539Notes

Reaction equation

HRID 621539 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:20]([C:23]1[CH:24]=[C:25]([CH:38]=[CH:39][CH:40]=1)[CH:26]=[C:27]([C:35]([CH3:37])=O)[C:28]([O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1)=[O:29])([O-:22])=[O:21].[NH3:41]>C(O)C>[CH3:5][C:3]1[NH:41][C:35]([CH3:37])=[C:27]([C:28]([O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)=[O:29])[CH:26]([C:25]2[CH:38]=[CH:39][CH:40]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 125291772-[N-(4-chlorobenzyl)-N-methylamino]-ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Product 1

HCID 141000933-[2-[N-(4-chlorobenzyl)-N-methylamino]ethyl] 5-cyclopropylmethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.0 g (35 mmol) of 2-[N-(4-chlorobenzyl)-N-methylamino]-ethyl acetoacetate, 10.2 g (35 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 2.9 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 and crystallized from methanol to afford 3-[2-[N-(4-chlorobenzyl)-N-methylamino]ethyl] 5-cyclopropylmethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (11.0 g, 56.3%) as yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-b139cdff21cb47c79f58df178d5965b9
Source dataset
uspto-grants-1989_04
Patent number
US04824855

Reaction notes

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