Potassium Carbonate → 4-Chloro-5-(3,3-difluoropyrrolidin-1-yl)-2-nitroaniline

HRID 1258635Notes

Reaction equation

HRID 1258635 reaction equation
Cl.[F:2][C:3]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]1[C:22](Cl)=[CH:21][C:19]([NH2:20])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1>CN(C=O)C>[Cl:15][C:16]1[C:22]([N:5]2[CH2:6][CH2:7][C:3]([F:8])([F:2])[CH2:4]2)=[CH:21][C:19]([NH2:20])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 679578464-Chloro-5-(3,3-difluoropyrrolidin-1-yl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

3,3-Difluoropyrrolidine hydrochloride (3.12 g, 21.7 mmol) followed by potassium carbonate (4.00 g, 29.0 mmol) were added to 4,5-dichloro-2-nitroaniline (3.00 g, 14.5 mmol) in DMF (60 mL). The reaction mixture was stirred at 130° C. over the weekend. After cooling the reaction mixture was poured into ice-water and extracted with EtOAc. The combined organic layers were washed with water, dried, concentrated and the crude was purified by chromatography to give the sub-title compound.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-ef18b217077e48dba0f367221bd342e7
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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