Acetic Acid → N-(2,4-Difluorophenyl)-3-nitropyridin-2-amine

HRID 1974323Notes

Reaction equation

HRID 1974323 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:13]=1[NH2:14].C(O)(=O)C>O>[F:11][C:12]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:13]=1[NH:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 97092,4-DifluoroanilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 12445346N-(2,4-Difluorophenyl)-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (7.9 g., 0.05 mole) 2-chloro-3-nitropyridine and 12.9 g. (0.10 mole) of 2,4-difluoroaniline was purged with nitrogen and heated in an oil bath to 110° C. when the temperature rose spontaneously to 135° C. Heating was continued to 145° C. when a second spontaneous temperature rise occurred requiring temperature control with ice. The maximum internal temperature was 185° C. After slight cooling, 40 ml. of acetic acid and 60 ml. of water was added. After stirring one hour the crystalline precipitate was collected (11.1 g., m.p. 110° C.) and recrystallized from hexane to give 2-(2,4-difluoroanilino)-3-nitropyridine, m.p. 112°-114° C.

Workup

  1. customrose spontaneously to 135° C
  2. temperatureHeating
  3. customwas continued to 145° C.
  4. customwas 185° C
  5. customwas collected (11.1 g., m.p. 110° C.)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-c64caf06273745c6abee1c0cfa78db7f
Source dataset
uspto-grants-1976_12
Patent number
US04000286

Reaction notes

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