Potassium Carbonate → HCID 27134398, compound

HRID 1014226Notes

Reaction equation

HRID 1014226 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:7][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 246995HCID 246995, compound

Product 1

HCID 27134398HCID 27134398, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-N-(4-methyl-3-nitrophenyl)acetamide (1.0 g, 4.39 mmol), potassium carbonate (3.63 g, 26.3 mmol), pyrrolidine (0.93 g, 13.2 mmol, Aldrich), and catalytic Kl (˜100 mg, Aldrich) in anhydrous THF (50 mL) was heated for 3 hrs at 60° C. The solvent was removed under reduced pressure, residue redissolved in dichloromethane (100 mL), washed with water (100 mL) and purified by column chromatography (dichloromethane to 10% methanol/dichloromethane) to provide N-(4-methyl-3-nitrophenyl)-2-(1-pyrrolidinyl)acetamide (0.86 g, 75%). ESIMS (M+H)+=264.

Workup

  1. customThe solvent was removed under reduced pressure, residue
  2. dissolutionredissolved in dichloromethane (100 mL)
  3. washwashed with water (100 mL)
  4. custompurified by column chromatography (dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-3bc2ebc8e23f4a6e9a045e7e3094b6f2
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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