N-Methoxy-2-phenyl-3,4-dihydroquinoline-1(2H)-carboxamide → 1-Methoxy-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 589090Notes

Reaction equation

[CH3:1][O:2][NH:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH:7]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][N:3]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:9][CH2:8][CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:6]3[C:4]1=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-methoxy-2-phenyl-3,4-dihydroquinoline-1(2H)-carboxamide (0.869 g, 3.08 mmol) in chloroform (23.2 mL) at 0° C. was with treated with [I,I-bis(trifluoroacetoxy)iodo]benzene (1.59 g, 3.69 mmol) in four portions over 20 min. The resulting mixture was stirred at 0° C. for 30 min and at room temperature for 30 min. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate solution (40 mL) and extracted with dichloromethane (50 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give a crude oil. Purification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes, the ethyl acetate containing 5% methanol) gave the desired product (0.576 g, 66%) as a racemic mixture. LCMS calculated for C17H17N2O2 (M+H)+: m/z=281.1. found: 281.1.

Workup

customat 0° C.
extractionextracted with dichloromethane (50 mL)
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude oil
customPurification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-f11325a45f9d4dd8a40aa9eb42591efc
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227985B2

Reaction notes

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