4-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrile

HRID 379126노트

반응식

HRID 379126 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[F:8]>C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

참가 물질

3

반응물 1

HCID 110133114-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

생성물 1

HCID 110124336-Amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrile수율 91.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 5.360 g (15.6 mmol) 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-quinoline-3-carbonitrile, 250 ml ethanol, and 17.67 g (78.2 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1½ hours and added ice water. Made basic with sodium bicarbonate. Stirred for 2 hours extracted with chloroform. Added brine to the separatory funnel to help separate layers. Stirred organic layer with Darco and dried with sodium sulfate. Filtered, stripped solvent and dried in vacuo, giving 4.460 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=312.9, 315.0.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 1½ hours
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. customAdded brine to the separatory funnel to help separate layers
  8. dry with materialStirred organic layer with Darco and dried with sodium sulfate
  9. filtrationFiltered
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-f174ef56158346a7ad18df2ebdcacaa0
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297258B1

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