Cyclohexanemethylamine → (7-Bromo-3-nitroquinolin-4-yl)cyclohexylmethylamine

HRID 9461

반응식

HRID 9461 반응식
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1>ClCCl>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 76688CyclohexanemethylamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

생성물 1

HCID 68820944(7-Bromo-3-nitroquinolin-4-yl)cyclohexylmethylamine수율 62.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under a nitrogen atmosphere, cyclohexylmethylamine (40.9 mL, 315 mmol) was added dropwise to a solution of 7-bromo-4-chloro-3-nitroquinoline (30.0 g, 105 mmol) in dichloromethane (524 mL). The reaction was stirred for 18 hours at ambient temperature and then concentrated under reduced pressure. Water (200 mL) was added to the residue, and the mixture was stirred for three hours. Acetonitrile was added; a precipitate formed. The solid was isolated by filtration, dried under a flow of air for two hours, and recrystallized from acetonitrile to provide 24.0 g of (7-bromo-3-nitroquinolin-4-yl)cyclohexylmethylamine as a yellow solid.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionWater (200 mL) was added to the residue
  3. stirringthe mixture was stirred for three hours
  4. additionAcetonitrile was added
  5. customa precipitate formed
  6. customThe solid was isolated by filtration
  7. customdried under a flow of air for two hours
  8. customrecrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-87647dbc841a4245be527a11092613db
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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