3-Chloro-4-fluoroaniline → 4-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 548430Notes

Reaction equation

HRID 548430 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[F:25])[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[F:25]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 110133114-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrileYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-quinoline-3-carbonitrile, 200 ml ethanol, and 3.75 g (25.8 mmol) 3-chloro-4-fluoroaniline was heated to reflux under N2. Removed heat at 3½ hours and added a solution of saturated sodium bicarbonate until mixture was basic. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solids, washed with water and dried in vacuo. Dissolved solids in 250 ml boiling ethyl acetate, stirred with Darco, and filtered. Stripped solvent and dried in vacuo, giving 6.036 g of yellow solid: mass spectrum (electrospray m/e): M+H=343.1, 345.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 3½ hours
  5. additionadded a solution of saturated sodium bicarbonate until mixture
  6. customStripped solvents and azeotroped with ethanol
  7. customcollected solids
  8. washwashed with water
  9. customdried in vacuo
  10. dissolutionDissolved solids in 250 ml
  11. filtrationfiltered
  12. customStripped solvent and dried in vacuo

Sources & evidence

ORD record
ord-23b3eed8c9004e408f964b741def0d03
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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