Potassium Carbonate → N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide

HRID 533464Notes

Reaction equation

HRID 533464 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].[H-].[Na+].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:3]([NH:11][C:12](=[O:14])[CH3:13])[CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-

Product 1

HCID 58098809N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamideYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-hydroxy-5-nitrophenyl)acetamide (870 mg, 4.44 mmol) in DMF (5 mL) was added NaH (196 mg, 5.32 mmol) and K2CO3 (2.11 g, 13.32 mmol), followed by 1-(2-chloroethyl)pyrrolidine hydrochloride (905 mg, 5.32 mmol). After heating at 100° C. for 20h, the solution was poured to ice, and was extracted with EtOAc, organic layer was washed with Sat. NaHCO3, brine, dried and concentrated to give N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide (430 mg).

Workup

  1. additionthe solution was poured to ice
  2. extractionwas extracted with EtOAc, organic layer
  3. washwas washed with Sat. NaHCO3, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d1a65f1c54b4bc6b776dfccd7943cc4
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

Loading…