Pyridine → HCID 13376456, compound

HRID 986650Notes

Reaction equation

HRID 986650 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH3:14])=[O:5].N1C=CC=CC=1.[F:28][CH2:29][C:30](Cl)=[O:31]>O1CCCC1>[F:28][CH2:29][C:30]([NH:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH3:14])=[O:5])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9663Fluoroacetyl chlorideHCID 13376448HCID 13376448, compound

Product 1

HCID 13376456HCID 13376456, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.3 g of N-(2-amino-5-nitrobenzoyl)-2-methyl-4-chloroaniline and 1.6 g of pyridine are dissolved in 60 ml of tetrahydrofuran, and 1.93 g of fluoroacetyl chloride are added dropwise thereto under ice-cooling and stirring. The mixture is stirred for 30 minutes under ice-cooling and further stirred at room temperature for 2 hours. The mixture is concentrated under reduced pressure to remove tetrahydrofuran. Water is added to the residue and crystalline precipitates are collected therefrom. The crystals are recrystallized from a mixture of dimethylformamide and ethanol (1:3). 3.6 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-2-methyl-4-chloroaniline are obtained as colorless needles.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture is stirred for 30 minutes under ice-
  3. temperaturecooling
  4. stirringfurther stirred at room temperature for 2 hours
  5. concentrationThe mixture is concentrated under reduced pressure
  6. customto remove tetrahydrofuran
  7. additionWater is added to the residue
  8. customcrystalline precipitates
  9. customare collected
  10. customThe crystals are recrystallized from a mixture of dimethylformamide and ethanol (1:3)

Sources & evidence

ORD record
ord-40ece020593443a89f1225aae194f604
Source dataset
uspto-grants-1987_12
Patent number
US04714702

Reaction notes

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