4-[(3-Chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-(3-chlorophenylamino)quinoline-3-carbonitrile

HRID 1934988Notes

Reaction equation

HRID 1934988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1>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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 1

HCID 224666744-[(3-Chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 224666926-Amino-4-(3-chlorophenylamino)quinoline-3-carbonitrileYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.30 g (19.4 mmol) 4-[(3-chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile, 300 ml ethanol, and 21.9 g (97 mmol) SnCl2 dihydrate were heated to reflux under N2. Removed heat at 2.5 hours, added ice water and made basic with sodium bicarbonate. Stirred for 2 hours and extracted with chloroform. Dried organic layer with sodium sulfate, filtered, stripped solvent and dried residue in vacuo, giving 5.74 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=295.1, 297.1.

Workup

  1. temperaturewere heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 2.5 hours
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. filtrationDried organic layer with sodium sulfate, filtered

Sources & evidence

ORD record
ord-1e989240626f40388b6d74998603f2f5
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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