2-(3-Bromo-2-methyl-phenyl)-3-(3-dimethylamino-phenylamino)-acrylic acid ethyl ester → 3-(3-Bromo-2-methyl-phenyl)-7-dimethylamino-1H-quinolin-4-one

HRID 2188755Notes

Reaction equation

C(O[C:4](=[O:25])[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[C:18]=1[CH3:24])=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([CH3:16])[CH3:15])[CH:9]=1)C>O>[Br:23][C:19]1[C:18]([CH3:24])=[C:17]([C:5]2[C:4](=[O:25])[C:13]3[C:8](=[CH:9][C:10]([N:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To 2-(3-Bromo-2-methyl-phenyl)-3-(3-dimethylamino-phenylamino)-acrylic acid ethyl ester (100 mg, 0.248 mmol) was added 4 g polyphosphoric acid. This stirred at 140° C. for 10 minutes. 50 ml water was added and the mixture was stirred. The resulting precipitate was filtered and washed with water. The filtrate was extracted with 10% methanol/dichloromethane solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was combined with the precipitate and purified by flash chromatography (gradient elution 2 to 5% methanol/dichloromethane) to yield 3-(3-Bromo-2-methyl-phenyl)-7-dimethylamino-1H-quinolin-4-one (22 mg, 0.062 mmol). MS (ESI) 357.0 (M+H)+.

Workup

stirringthe mixture was stirred
filtrationThe resulting precipitate was filtered
washwashed with water
extractionThe filtrate was extracted with 10% methanol/dichloromethane solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography (gradient elution 2 to 5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-ae387dc9e7b7421a98733e64b70c1459
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324211B2

Reaction notes

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