Potassium Carbonate → 1-(3-nitrophenyl)pyrrolidin-2-one

HRID 2086068Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+]>N1CCCC1=O.O.[Cu]>[N+:8]([C:4]1[CH:3]=[C:2]([N:8]2[CH2:4][CH2:3][CH2:2][C:11]2=[O:14])[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 200 °C

Procedure

A suspension of 1-iodo-3-nitrobenzene (24.9 g, 0.1 mol), copper bronze (320 mg, 5 mmol) and potassium carbonate (15.2 g, 0.11 mol) in 2-pyrrolidinone was heated under a stream of nitrogen at 200° C. for 45 minutes. The reaction was cooled to ambient temperature, diluted with water (2000 ml) and extracted with diethyl ether (800 ml). The organic phase was then washed with water (2×800 ml), brine and dried over anhydrous sodium sulphate containing decolourising charcoal (2 g). Filtration and evaporation to dryness gave a yellow solid which was triturated with isohexane to give 1-(3nitrophenyl)pyrrolidin-2-one as a yellow powder (3.0 g, 15%). δH (360 MHz, CDCl3) 2.19-2.27 (2H, m), 2.67 (2H, t, J 8), 3.94 (2H, t, J 7), 7.54 (1H, t, J 8), 8.00 (1H, ddd, J 8, 2 and 1), 8.22 (1H, ddd, J 8, 2 and 1), 8.35 (1H, t, J 2).

Workup

temperatureThe reaction was cooled to ambient temperature
extractionextracted with diethyl ether (800 ml)
washThe organic phase was then washed with water (2×800 ml), brine
dry with materialdried over anhydrous sodium sulphate containing decolourising charcoal (2 g)
filtrationFiltration and evaporation to dryness
customgave a yellow solid which
customwas triturated with isohexane

Sources & evidence

ORD record: ord-d1aaaf6aed00459c9746ca753ec0d76b
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723735B1

Reaction notes

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