Water → 3-(2,4-Difluorophenylamino)-4-nitrobenzonitrile

HRID 1087199Notes

Reaction equation

HRID 1087199 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[F:13][C:14]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:15]=1[NH2:16].C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=O)C>[F:13][C:14]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:15]=1[NH:16][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 97092,4-DifluoroanilineHCID 11430Potassium CarbonateHCID 149730283-Chloro-4-nitrobenzonitrile

Product 1

HCID 198177173-(2,4-Difluorophenylamino)-4-nitrobenzonitrileYield 46.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-chloro-4-nitrobenzonitrile (5 g), 2,4-difluoroaniline (17.7 g), cupric oxide (0.5 g) and potassium carbonate (4.5 g) was stirred for 5 hours at 200° C. To the mixture were added water (100 ml) and ethyl acetate (200 ml). The organic layer was separated, washed with 3N hydrochloric acid and water, dried, and evaporated to dryness. The oil (10 g) was purified by column chromatography on silica gel (200 g) eluting with toluene to give red crystals of 3-(2,4-difluorophenylamino)-4-nitrobenzonitrile (3.5 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with 3N hydrochloric acid and water
  3. customdried
  4. customevaporated to dryness
  5. customThe oil (10 g) was purified by column chromatography on silica gel (200 g)
  6. washeluting with toluene

Sources & evidence

ORD record
ord-3de87cd80db34c92a0a5c86685068280
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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