Tetronic acid → HCID 136452090, compound

HRID 862614Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=1)=O.[CH2:25]1[C:30](=[O:31])[O:29][CH2:28][C:26]1=O>S(=O)(=O)(O)O.C(O)(=O)C>[CH3:22][O:21][C:19]1[C:18]([O:23][CH3:24])=[CH:17][C:3]2[C:4]([C:6]3[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=3)=[C:25]3[C:30](=[O:31])[O:29][CH2:28][C:26]3=[N:1][C:2]=2[CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

One drop of conc. sulfuric acid was added to a mixture of 2-amino-4,5,3',5'-tetramethoxy-4'-hydroxybenzophenone (0.333 g), tetronic acid (tetrahydrofuran-2,4-dione) (0.11 g) and acetic acid (10 ml), and the mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residual oil was poured into water, neutralized with an aqueous saturated sodium bicarbonate solution and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 6,7-dimethoxy-9-(4-hydroxy-3,5-dimethoxyphenyl)furo[3,4-b]quinoline -1(3H)-one (0.349 g, 88%) which was then recrystallized from methanol. Pale yellow needles. mp. 247°-248° C.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionThe residual oil was poured into water
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-bc349a17cbab4b17bdedcfd6a5b7bf15
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719157

Reaction notes

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