4-Chloro-6-nitroquinoline-3-carbonitrile → 4-[(3-Chloro-4thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 548436Notes

Reaction equation

HRID 548436 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:21]>C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrileHCID 234380833-Chloro-4-(phenylsulfanyl)aniline

Product 1

HCID 1317214944-[(3-Chloro-4thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrileYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-quinoline-3-carbonitrile, 250 ml ethanol, and 6.07 g (25.6 mmol) 3-chloro-4-thiophenoxyaniline was heated to reflux under N2. Removed heat at about 8 hours, made basic with saturated sodium bicarbonate, stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected solids. Washed with water and dried in vacuo. Dissolved nearly completely in 400 ml ethyl acetate, stirred with Darco and filtered. Stripped solvent and boiled in hexane to remove last of the excess aniline. Dried in vacuo, giving 6.90 g of red solid: mass spectrum (electrospray m/e): M+H=433.1, 435.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at about 8 hours
  5. customazeotroped with ethanol
  6. customcollected solids
  7. washWashed with water
  8. customdried in vacuo
  9. dissolutionDissolved nearly completely in 400 ml ethyl acetate
  10. filtrationfiltered
  11. customto remove last of the excess aniline
  12. customDried in vacuo

Sources & evidence

ORD record
ord-32f0cdb4d9bb4d50a30e60c1a6dd57e3
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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