p-Toluidine → 1H-Pyrrolizin-1-one, 2,3-dihydro-2-[[(4-methylphenyl)amino]methyl]-

HRID 52197Notes

Reaction equation

C[N:2]([CH2:4][CH:5]1[CH2:12][N:11]2[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]1=[O:13])[CH3:3].[CH3:14][C:15]1[CH:21]=[CH:20]C(N)=[CH:17][CH:16]=1>>[CH3:14][C:15]1[CH:21]=[CH:20][C:3]([NH:2][CH2:4][CH:5]2[CH2:12][N:11]3[C:7](=[CH:8][CH:9]=[CH:10]3)[C:6]2=[O:13])=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 7813p-Toluidine

HCID 102196682-Dimethylaminomethyl-1, 2-dihydro-1-pyrrolizinone

Product 1

HCID 117764371H-Pyrrolizin-1-one, 2,3-dihydro-2-[[(4-methylphenyl)amino]methyl]-Yield 83%

Procedure

A solution of 17.5 g, compound (2) and 10 g 4-methylaniline was allowed to stand at room temperature for 12 hours. 22 g yellow solid was obtained after filtering. Recrystallized from ethanol, 19 g (5) was obtained as a white crystal, mp 112°-114° C., yield 83%.

Sources & evidence

ORD record: ord-21fd8035906d4459b94e4244a6df8a84
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616604

Reaction notes

Loading…