2-Pyrrolidone → 3-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 1664223Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[NH:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19]>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].[Cu]>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]

Participants

Conditions

Temperature: 150 °C

Procedure

The mixture of 3.37 g (13.7 mmol) 3-bromo-5-nitro-benzoic acid, 1.74 g (27.4 mmol, 2 eq) cuper powder, 3.18 ml (41 mmol, 3 eq) 2-pyrrolidinone and 1.89 g (13.7 mmol, 1 eq) potassium carbonate is stirred at 150° C. for 16 h. Another 10 ml 2-pyrrolidinone, 1.74 g (27.4 mmol, 2 eq) copper powder and 1.89 g (13.7 mmol, 1 eq) potassium carbonate are added and the mixture is again stirred vigorously for 5.5 h at 150° C. After cooling to rt the reaction is diluted with DCM and 5% aq potassium carbonate. Solids are filtered off and the aqueous layer is acidified with 10% aq potassium hydrogensulfate solution. Extraction with DCM, drying over sodium sulfate, and evaporation of the solvent at reduced pressure gives some product. On standing more product precipitates from the aqueous layer, is filtered off and dried in vacuum.

Workup

stirringthe mixture is again stirred vigorously for 5.5 h at 150° C
temperatureAfter cooling to rt the reaction
filtrationSolids are filtered off
extractionExtraction with DCM
dry with materialdrying over sodium sulfate, and evaporation of the solvent at reduced pressure
customgives some product
customprecipitates from the aqueous layer
filtrationis filtered off
customdried in vacuum

Sources & evidence

ORD record: ord-e738f1e6e86e41c487dc8577f9258ca3
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039455B2

Reaction notes

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