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

HRID 612093Notes

Reaction equation

HRID 612093 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-3-quinolinecarbonitrile, 250 ml ethanol and 2.55 ml (25.8 mmol) 3,4-difluoroaniline was heated to reflux under N2. Removed heat at 3.5 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 3.5 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-932a788b8ff44403a736b6a4b5520d20
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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