Nitric Acid → 2,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1506576Notes

Reaction equation

[F:1][C:2]1([F:14])[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[NH:4][C:3]1=[O:13].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>O>[F:14][C:2]1([F:1])[O:7][C:6]2[CH:8]=[C:9]([F:12])[C:10]([N+:20]([O-:22])=[O:21])=[CH:11][C:5]=2[NH:4][C:3]1=[O:13]

Participants

Conditions

Temperature: 2.5 °C

Procedure

2,2,7-trifluoro-2H-benzo[b][1,4]oxazin-3(4H)-one (2.5 g, 12.31 mmol) was dissolved in sulfuric acid (40 ml, 750 mmol). The reaction mixture was cooled to 0-5° C. Slowly nitric acid (1.761 ml, 39.7 mmol) was added dropwise and the temperature was maintained between 0-5° C. The reaction mixture was stirred for 30 min at this temperature. Then the reaction mixture was added dropwise to vigorously stirred cold water. A solid was formed, extraction with Dichloromethane. The combined extracts were dried over Na2SO4, and concentrated to yield 2.56 g of the title compound as brown solid.

Workup

temperaturethe temperature was maintained between 0-5° C
customA solid was formed
extractionextraction with Dichloromethane
dry with materialThe combined extracts were dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-147bc78e73354749b9e19b840fa6b3cf
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220268B2

Reaction notes

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