Formic Acid → 4,7-Dihydroxy-3-(3-nitrobenzyl)-2-oxo-2H-1-benzopyran

HRID 1046779Notes

Reaction equation

[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]([OH:12])=[CH:11][C:6]=2[O:5][C:4](=[O:13])[CH:3]=1.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].C(N(CC)CC)C.C(O)=O.Cl>C(OCC)(=O)C>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]([OH:12])=[CH:11][C:6]=2[O:5][C:4](=[O:13])[C:3]=1[CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4,7-Dihydroxy-2-oxo-2H-1-benzopyran (500 mg, 2.81 mmol) and 3-nitrobenzaldehyde (424 mg, 2.81 mmol) were added to a mixture of triethylamine (1.57 mL, 11.23 mmol) and formic acid (1.07 mL, 28.07 mmol), and the obtained mixture was stirred at 100° C. for 2 hours. A 5N hydrochloric acid aqueous solution was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate, and then concentrated under reduced pressure to yield the title compound (300 mg, 34%) as a pale yellow solid.

Workup

extractionThe organic extract
washwas washed with saturated saline
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2c4c20da90854020a663be56d57293ef
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569378B2

Reaction notes

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