Stannous Chloride → 6-Amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile

HRID 379128Notes

Reaction equation

HRID 379128 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.Cl[Sn]Cl>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

4

Reactant 2

HCID 24479Stannous ChlorideHCID 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-quinoline-3-carbonitrile, 155 ml ethanol, and 9.47 g (42.0 mmol) SnCl2 dehydrate 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-b8c6a470cfc24d97b234dd5f148dae2d
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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