Water → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394211Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](N)=[O:19])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28].[OH-].[Na+].O.Cl[O-].[Na+].[O:36]1CCOC[CH2:37]1>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]([O:36][CH3:37])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]

Participants

Conditions

Temperature: 60 °C

Procedure

To 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxamide (920 mg) in dioxane (330 mL) was added 5N NaOH (10 mL) and water (41 mL) followed by sodium hypochlorite (19.3 mL of a 10-13% aqueous solution) and the reaction mixture heated to 60° C. for 2 h. The cooled reaction mixture was then poured into brine and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.61-7.32 (m, 8H); 6.48 (d, J=2.1 Hz, 1H); 6.45 (d, J=9.7 Hz, 1H); 5.73 (d, J=2.1 Hz, 1H; 4.00 (br.s, 2H). Mass spectrum: m/z 415 (M+H).

Workup

customThe cooled reaction mixture
extractionextracted into ethyl acetate
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with hexane/ethyl acetate

Sources & evidence

ORD record: ord-aa8ce7a44c98442297a7d7da7dc255cf
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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