Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate → Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394209Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate (1.25 g)(contaminated with 20% of the E isomer) was dissolved in dimethylformamide(36 mL) and the solution degassed with argon. Copper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added and the mixture heated to 80° C. for 30 min. The reaction mixture was poured into 5% ammonium hydroxide solution and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 80% hexane: 20% ethyl acetate to give the title compound.

Workup

customthe solution degassed with argon
additionCopper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added
additionThe reaction mixture was poured into 5% ammonium hydroxide solution
extractionextracted into ethyl acetate
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with 80% hexane

Sources & evidence

ORD record: ord-50f029a29e7c40aa80bf4bac3d5fbc1b
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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