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

HRID 548429ノート

反応式

HRID 548429 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4166f67997d74a30981bd05fc67a7bf2
出典データセット
uspto-grants-2011_05
特許番号
USRE042376E1

反応ノート

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