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

HRID 1935008Notes

Reaction equation

HRID 1935008 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>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

5

Reactant 3

HCID 297MethaneHCID 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 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
  13. customgiving ethyl acetate
  14. filtrationfiltered
  15. customdried in vacuo

Sources & evidence

ORD record
ord-b9866a3e3b3f4694ba4c7b38c9a76bbc
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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