Methyl 4-(2-oxopyrrolidin-1-yl)benzoate → 1-(4-Methoxycarbonyl-2-nitrophenyl)pyrrolidin-2-one

HRID 1635552Notes

Reaction equation

HRID 1635552 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[CH:7][CH:6]=1)=[O:4].F[B-](F)(F)F.[O:22]=[N+:23]=[O:24]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[C:9]([N+:23]([O-:24])=[O:22])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 757827Methyl 4-(2-oxopyrrolidin-1-yl)benzoateHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 106830071-(4-Methoxycarbonyl-2-nitrophenyl)pyrrolidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

An ice-cold mixture of the above ester (2.0 g, 9.1 mmol) in 30 mL of dichloromethane was treated with nitronium tetrafluoroborate (2.5 g, 18.8 mmol). The resulting mixture was stirred at 10° C. for 2 h and then at ambient temperature for 4 h. The reaction mixture was quenched with water (20 mL) and the organic layer was evaporated under vacuum. The white solid precipitate was collected by filtration, washed with water and dried to give 2.2 g (92%) of 1-(4-methoxycarbonyl-2-nitrophenyl)pyrrolidin-2-one, mp 159-161° C. (chloroforn/ether).

Workup

  1. waitat ambient temperature for 4 h
  2. customThe reaction mixture was quenched with water (20 mL)
  3. customthe organic layer was evaporated under vacuum
  4. filtrationThe white solid precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9ec9cb610b734f5b982a2c9f3c33e673
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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