Methyl 3-aminocrotonate → Methyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

HRID 485073노트

반응식

HRID 485073 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH:7]=[C:8]([P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])[C:9]([CH3:11])=O)([O-:3])=[O:2].[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25]>C(O)(C)C>[CH3:14][O:13][P:12]([O:15][CH3:16])([C:8]1[CH:7]([C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([CH3:28])[NH:21][C:9]=1[CH3:11])=[O:17]

참가 물질

4

반응물 2

HCID 643918Methyl 3-aminocrotonateHCID 53986679Dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate

생성물 1

HCID 10596880Methyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate수율 44.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a mixture of 1.85 grams of dimethyl 1-(3-nitrobenzylidene)-acetonylphosphonate and 0.75 gram of methyl 3-aminocrotonate was added 25 ml of isopropanol and the mixture was heated to reflux for four hours with stirring. The reaction mixture was concentrated in vacuo, to the residue was added ether, the resulting crystals were collected by filtration, and recrystallized from ethyl acetate to afford 1.08 grams (yield 42%) of methyl 5-dimethoxyphosphinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, melting point 221°-3° C.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for four hours
  3. concentrationThe reaction mixture was concentrated in vacuo, to the residue
  4. additionwas added ether
  5. filtrationthe resulting crystals were collected by filtration
  6. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-d22c3e6da8624db5a853704c4a307f39
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04535073

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