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

HRID 1935010Notes

Reaction equation

HRID 1935010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:29]#[N:30])=[C:16]2[NH:15][C:4]1[CH:5]=[CH:6][C:7]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 1

HCID 1317214944-[(3-Chloro-4thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 1317214936-Amino-4-[(3-chloro-4thiophenoxyphenyl)amino]-3-quinolinecarbonitrileYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.753 g (15.6 mmol) 4-[(3-chloro-4-thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, and 17.66 g (78.0 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 2 hours, added large volume of ice water, and made basic with sodium bicarbonate. Stirred for 2 hours and with mixture still basic, extracted with chloroform. Stirred organic layer with Darco, dried with sodium sulfate, filtered, stripped solvent and dried in vacuo, giving 5.996 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=403.1, 405.1.

Workup

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

Sources & evidence

ORD record
ord-6e5c823f881f4805af68b3efa4589468
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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