4-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

HRID 1935007Notes

Reaction equation

HRID 1935007 reaction equation
[F: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]([F:1])[CH:3]=1

Participants

3

Reactant 1

HCID 224666064-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrileYield 88.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.53 g (13.9 mmol) 4-[(3,4-difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile, 200 ml ethanol and 15.72 g (69.4 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1.5 hours, added ice water and made basic with sodium bicarbonate. Stirred for 2 hours and extracted with chloroform. Stirred organic layer with Darco, dried with sodium sulfate and filtered. Stripped solvent and dried in vacuo, giving 3.660 g of yellow-green solid: mass spectrum (electrospray m/e): M+H=297.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 1.5 hours
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. dry with materialStirred organic layer with Darco, dried with sodium sulfate
  8. filtrationfiltered
  9. customStripped solvent and dried in vacuo

Sources & evidence

ORD record
ord-94e69f1641fc411490b04e979ac73022
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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