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

HRID 548425Notes

Reaction equation

HRID 548425 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-quinoline-3-carbonitrile, 300 ml ethanol, and 21.9 g (97 mmol) SnCl2 dihydrate were heated to reflux under N2. Removed heat at 2½ 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 2½ hours
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. filtrationDried organic layer with sodium sulfate, filtered

Sources & evidence

ORD record
ord-c8dcd70460c04909a8a5aaed861b6b99
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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