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

HRID 379130Notes

Reaction equation

HRID 379130 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-quinoline-3-carbonitrile, 200 ml ethanol and 15.72 g (69.4 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1½ 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 1½ 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-bf1dd0ae5e284de387c3d0681a1c437b
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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