Isatoic Anhydride → HCID 58601126, compound

HRID 2243411Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=O)[CH3:4].[C:20]12[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:25]C(=O)O[C:21]2=[O:22]>CC(N(C)C)=O>[CH2:3]([O:5][C:6]([C:7]1[C:21](=[O:22])[C:20]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:8]=1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:19])[CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium hydride (0.92 g, 0.023 mol; 60% suspension in mineral oil) was added portionwise to a stirred solution of 3-(4-nitrophenyl)-3-oxopropionic acid ethyl ester (5.46 g, 0.023 mol) in dimethylacetamide (20 mL) at room temperature. A solution of isatoic anhydride (3.4 g, 0.02 mol) in dimethylacetamide (20 mL) was added to this solution. The reddish mixture was stirred at 120° C. for 30 min and then the solvent was concentrated in vacuo. The crude solid was partitioned between water and ethyl acetate and the organic phase then separated. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to leave a residue which was washed once with cold tert-butylmethyl ether to yield 2-(4-nitrophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (1.61 g, 28%) as a white solid, LCMS m/z 339.33 [M+H]+ @ RT 1.16 min, 100% purity.

Workup

concentrationthe solvent was concentrated in vacuo
customThe crude solid was partitioned between water and ethyl acetate
customthe organic phase then separated
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated in vacuo
customto leave a residue which
washwas washed once with cold tert-butylmethyl ether

Sources & evidence

ORD record: ord-9b86c2265d2b4385a6d2a5b716b6a965
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674906B2

Reaction notes

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