4-Chlorotoluene → 1-(4-methylphenyl)pyrrolidin-2-one

HRID 1883338Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.[NH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].Cl[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1>[Cu]I>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 140 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (20 mg, 0.105 mmol, 5.1 mol %), K2CO3 (600 mg, 4.34 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (26 μL, 0.217 mmol, 11 mol %), 2-pyrrolidinone (155 μL, 2.04 mmol) and 4-chlorotoluene (1.0 mL, 8.44 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 140° C. for 42 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:7; 20 mL fractions). Fractions 10-20 provided 223 mg (62% yield) of the product as white crystals. The 1H NMR spectrum was in accord with that reported by Boeyens et al. Billing, D. G.; Boeyens, J. C. A.; Denner, L.; Du Plooy, K. E.; Long, G. C.; Michael, J. P. Acta Cryst. (B) 1991, B47, 284.

Workup

customevacuated
customThe Schlenk tube was sealed
temperatureThe resulting suspension was cooled to room temperature
filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
concentrationThe filtrate was concentrated
customthe residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:7; 20 mL fractions)

Sources & evidence

ORD record: ord-b0f2add0ead14821a31212b34fa595d3
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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