3-Nitrobenzaldehyde → Nicardipine Impurity 19

HRID 568933

반응식

HRID 568933 반응식
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:8]/[C:9](/[CH3:18])=[CH:10]\[C:11]([O:13][CH2:14][CH2:15][C:16]#[N:17])=[O:12].[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20]>C(O)(C)C>[C:16]([CH2:15][CH2:14][O:13][C:11]([C:10]1[CH:25]([C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:2]([C:1]([OH:7])=[O:6])=[C:3]([CH3:5])[NH:8][C:9]=1[CH3:18])=[O:12])#[N:17]

참가 물질

5

반응물 3

HCID 74493-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 136714102-Cyanoethyl 3-aminocrotonate

생성물 1

HCID 10429284Nicardipine Impurity 19수율 88.4%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

10.3 g of 3-nitratopropyl acetoacetate, 7.7 g of 2-cyanoethyl 3-aminocrotonate and 7.6 g of 3-nitrobenzaldehyde in 76 ml of isopropyl alcohol were heated at reflux for 6.5 hours, and cooled on ice. The crystals which precipitated were collected by filtration, dried, applied to a silica gel column chromatography (eluent: dichloromethane) and recrystallized from ethanol to give 16.4 g of 2,6-dimethyl-4-(3-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(3-nitratopropyl) ester.

후처리

  1. temperatureat reflux for 6.5 hours
  2. temperaturecooled on ice
  3. customThe crystals which precipitated
  4. filtrationwere collected by filtration
  5. customdried
  6. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-cf05da0d5c2c4a7cb1ab8b92df4a8cd5
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730052

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