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

HRID 548435Notes

Reaction equation

HRID 548435 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-quinoline-3-carbonitrile, 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-241fec51bf2d4289b9a89fe897b731ed
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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