3-Nitrobenzaldehyde → 2-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

HRID 1759053노트

반응식

HRID 1759053 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])=[O:17])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 814132-Ethoxyethyl acetoacetate

생성물 1

HCID 545745632-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 3-nitrobenzaldehyde (4.54 g), 2-ethoxyethyl acetoacetate (5.23 g) and piperidine (85.2 mg) in benzene (15 ml) was refluxed under azeotropic dehydration for 3 hours. The resultant mixture was washed with water, an aqueous solution saturated with sodium chloride and water in turn, dried and concentrated to give an oil of 2-ethoxyethyl 2-(3-nitrobenzylidene)acetoacetate. To this oily product was added ethyl 3-amino-4,4-diethoxycrotonate (6.5 g). The mixture was heated at 110° C. for about 3 hours. The reaction mixture was dissolved in ethyl acetate and washed with water twice and dried. The solvent was removed from the mixture to give an oil (15.58 g). This oil was subjected to column chromatography on silica gel with an eluent (a mixture of 10 parts of benzene and one part of ethyl acetate by volume) to give an oily substance (8.09 g). This oily substance (0.93 g) was treated with a mixture of n-hexane and diethyl ether to give crystals, which were further recrystallized from a mixture of n-hexane and diethyl ether to give yellow granules (565.2 mg) of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 99° to 100° C.

후처리

  1. temperaturewas refluxed under azeotropic dehydration for 3 hours
  2. washThe resultant mixture was washed with water
  3. dry with materialan aqueous solution saturated with sodium chloride and water in turn, dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0f509743b1834c8d9b0eab338c080b90
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04338322

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