3,4-Difluoroaniline → 4-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 548434Notes

Reaction equation

HRID 548434 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].[F:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH2:21]>C(O)C>[F: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 774693,4-DifluoroanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224666064-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrileYield 71.6%

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 2.55 ml (25.8 mmol) 3,4-difluoroaniline was heated to reflux under N2. Removed heat at 3½ hours and made basic with saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solids and air dried. Washed with water and dried in vacuo. Dissolved in ethyl acetate, stirred with Darco, filtered, stripped solvent and dried in vacuo, giving 5.02 g of yellow solid: mass spectrum (electrospray m/e): M+H=327.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 3½ hours
  5. customazeotroped with ethanol
  6. customcollected solids and air
  7. customdried
  8. washWashed with water
  9. customdried in vacuo
  10. dissolutionDissolved in ethyl acetate
  11. filtrationfiltered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-e8a97bc5c46146caabd8320c5647d5b4
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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