Acetic Acid → 2-Chloroethyl 2-[(2-nitrophenyl)methylidene]-3-oxobutanoate

HRID 1759050Notes

Reaction equation

HRID 1759050 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][Cl:21])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][Cl:21])=[O:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 1086052-Chloroethyl acetoacetate

Product 1

HCID 540729262-Chloroethyl 2-[(2-nitrophenyl)methylidene]-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-nitrobenzaldehyde (4.536 g), 2-chloroethyl acetoacetate (4.94 g) and piperidine (110 mg) in benzene (18 ml) and acetic acid (360 mg) was refluxed for an hour under azeotropic dehydration. The reaction mixture was washed with water and dried. The solvent was distilled off to give an reddish oil of 2-chloroethyl 2-(2-nitrobenzylidene)acetoacetate, and thus obtained oil was treated with ethyl 3-amino-4,4-diethoxycrotonate (7.1 g) to give yellow granules of 2-chloroethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 82° to 84° C. (recrystallized from diisopropyl ether).

Workup

  1. temperaturewas refluxed for an hour under azeotropic dehydration
  2. washThe reaction mixture was washed with water
  3. customdried
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-13b0ee3094b046f1a56b86c106b47677
Source dataset
uspto-grants-1982_07
Patent number
US04338322

Reaction notes

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