p-Toluenesulfonic acid → 7-(2,5-dimethyl-pyrrol-1-yl)-3,4-dihydro-1H-quinolin-2-one

HRID 519076Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:18][C:17]1[N:1]([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]3)=[CH:4][CH:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-amino-3,4-dihydroquinolin-2(1H)-one (3.0 g, 18.50 mmol), hexane-2,5-dione (3.0 g, 25.9 mmol) and 4-methylbenzenesulfonic acid (3.2 g, 18.50 mmol) in toluene (40 mL) was stirred at 100° C. for 30 min. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (eluting with 10% EtOAc in petroleum ether) to give 7-(2,5-dimethyl-pyrrol-1-yl)-3,4-dihydro-1H-quinolin-2-one (3.0 g, 67%). 1H NMR (CDCl3, 400 MHz): δ 8.72 (brs, 1H), 7.23 (d, J=8.0 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 6.67 (s, 1H), 5.89 (s, 2H), 3.02 (t, J=8.0 Hz, 2H), 2.68 (m, 2H), 2.03 (s, 6H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
concentrationconcentrated in vacuo
customthe residue was purified by flash column chromatography on silica gel (eluting with 10% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-af5e672c7d664a12a737049b8c8da5e6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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