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

HRID 548431Notes

Reaction equation

HRID 548431 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-4ed6640329ff4ce0ab9d960408c9f16b
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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