Trifluoroacetic acid → 6-Methyl-5-nitro-1H-isochromen-1-one

HRID 1161180Notes

Reaction equation

[N+:1]([C:4]1[C:13]([CH2:14]C(OC(C)(C)C)=O)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][O:8][C:9]2=[O:22])([O-:3])=[O:2].FC(F)(F)C(O)=O.N1C2C(=CC=CC=2)C=CC=1>C(OC(=O)C)C>[CH3:14][C:13]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:22])[O:8][CH:7]=[CH:6]2

Participants

Conditions

Temperature: 120 °C

Procedure

A microwave vial was charged with tert-butyl 2-(5-nitro-1-oxo-1H-isochromen-6-yl)acetate (800.0 mg, 0.002620 mol), trifluoroacetic Acid (2 mL, 0.02 mol) and subjected to microwave at 100° C. for 20 minutes. The starting material became converted into the corresponding acid. TFA was removed under reduced pressure and the residue was again taken a microwave tube and quinoline (2 mL, 0.02 mol) was added and heated at 120° C. for 20 minutes. The reaction went to completion and ethylacetate (50 mL) was added and washed with 10 mL of 6N HCl. The HCl layer was extracted with ethyl acetate (50 mL) and the combined organic layers were washed with water, brine and dried. The solvent was removed and the brown solid residue was purified by flash chromatography to yield the pure product as a white solid. MS m/z=206.4 (M+H) 1H-NMR (400 MHz, DMSO-d6) δ 8.29 (d, J=8.19 Hz, 1H), 7.71-7.69 (m, 2H), 6.57 (d, J=6.02 Hz, 1H), 2.45 (s, 3H).

Workup

customTFA was removed under reduced pressure
additionwas added
washwashed with 10 mL of 6N HCl
extractionThe HCl layer was extracted with ethyl acetate (50 mL)
washthe combined organic layers were washed with water, brine
customdried
customThe solvent was removed
customthe brown solid residue was purified by flash chromatography

Sources & evidence

ORD record: ord-53fe8b51eb2d43fda909fdbb9d8cc233
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

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