4-[(4-Bromophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile

HRID 1935004Notes

Reaction equation

HRID 1935004 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:22]#[N:23])=[CH:4][CH:3]=1>C(O)C>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:22]#[N:23])=[C:9]2[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 224667624-[(4-Bromophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 224665976-Amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrileYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.10 g (8.40 mmol) 4-[(4-bromophenyl)amino]-6-nitro-3-quinolinecarbonitrile, 155 ml ethanol, and 9.47 g (42.0 mmol) SnCl2 dihydrate was heated to reflux under N2. After 4 hours, removed heat and added ice water. Made basic with sodium bicarbonate and stirred for 2 hours. With mixture still basic, extracted with chloroform, stirred organic layer with Darco and dried with sodium sulfate. Filtered, stripped solvent and dried in vacuo, giving 2.265 g of brown-yellow solid: mass spectrum (electrospray m/e): M+H=339.0, 341.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved
  4. temperatureheat
  5. additionadded ice water
  6. extractionWith mixture still basic, extracted with chloroform
  7. stirringstirred organic layer with Darco
  8. dry with materialdried with sodium sulfate
  9. filtrationFiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-e867ff867a03458580d89b4e58c3b736
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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