2-Aminobenzonitrile → 4-(2-Cyanophenylamino)-3-ethoxycarbonyl-5,8-difluoroquinoline

HRID 266075Notes

Reaction equation

HRID 266075 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19](#[N:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH2:22]>CC(O)C>[C:19]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:27]

Participants

4

Reactant 2

HCID 729132-AminobenzonitrileHCID 17040076Ethyl 4-chloro-5,8-difluoroquinoline-3-carboxylate

Product 1

HCID 190324854-(2-Cyanophenylamino)-3-ethoxycarbonyl-5,8-difluoroquinolineYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The reaction mixture of 102.0 mg (0.37 mmol) of 4-chloro-3-ethoxycarbonyl-5,8-difluoroquinoline and 53.0 mg (0.44 mmol) of anthranilonitrile in 2.0 mL of 2-propanol was refluxed for 2 h and cooled down. The yellow precipitate was filtered, washed with cold 2-propanol, and dried in oven at 40° C. overnight to give 84.5 mg (65%) of the title compound.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled down
  3. filtrationThe yellow precipitate was filtered
  4. washwashed with cold 2-propanol
  5. customdried in oven at 40° C. overnight

Sources & evidence

ORD record
ord-e0989a7a2a27465f80b8e8b337745bd8
Source dataset
uspto-grants-1997_07
Patent number
US05650415

Reaction notes

Loading…