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

HRID 612086Notes

Reaction equation

HRID 612086 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.360 g (15.6 mmol) 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, and 17.67 g (78.2 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1.5 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.

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. 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

Sources & evidence

ORD record
ord-7c08c5b8a9c4478e8c178a752cbf0caf
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…