Potassium Carbonate → 1-(5-Amino-2-chloro-4-nitro-phenyl)-pyrrolidine-3-carbonitrile

HRID 1258661Notes

Reaction equation

HRID 1258661 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]#[N:14])[CH2:9]1.[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.CCOC(C)=O>[NH2:20][C:19]1[C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:16]([Cl:15])=[C:22]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]#[N:14])[CH2:9]2)[CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 42614784Pyrrolidine-3-carbonitrile hydrochloride

Product 1

HCID 679578281-(5-Amino-2-chloro-4-nitro-phenyl)-pyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (2.93 g, 21.3 mmol) was added to a mixture of pyrrolidine-3-carbonitrile hydrochloride (1.41 g, 10.6 mmol) and 4,5-dichloro-2-nitroaniline (2.00 g, 9.7 mmol) in DMF (8 mL). The reaction mixture was stirred at 120° C. overnight, diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, concentrated and the crude was purified by chromatography to give the sub-title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-c7a3c0b4fef241cdae3957138ff50280
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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