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

HRID 2061108Notes

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-970b906264874e5a988329139fbd20f4
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278465B2

Reaction notes

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