Ammonia → Diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(4-nitrophenyl)-3,5-pyridinedicarboxylate

HRID 364961Notes

Reaction equation

HRID 364961 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:34](=O)[CH3:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].[NH3:37]>C(O)C>[OH:17][C:10]1([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:34]([CH3:35])[NH:37]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13281Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl esterHCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate

Product 1

HCID 20189315Diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(4-nitrophenyl)-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-nitro-beta-oxobenzenepropanoate (4.74 g, 20 mmoles), ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate (5.26 g, 20 mmoles) and aqueous ammonia (2.2 ml, d0.88) were heated at reflux in ethanol (50 ml) for 1.5 hours. After cooling the product was filtered off and recrystallised from ethanol to give the title compound (2.6 g) mp 196°-7°.

Workup

  1. temperatureAfter cooling the product
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-3889b65d28b24086abd18ac50b41a51c
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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