Nitric Acid → HCID 14347815, compound

HRID 2291769Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.[C:12]([CH2:14][N:15]1[C:20]2[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=2[O:18][CH2:17][C:16]1=[O:26])#[N:13].[H-].[Na+]>S(=O)(=O)(O)O.O>[C:12]([CH2:14][N:15]1[C:20]2[CH:21]=[C:22]([N+:1]([O-:4])=[O:2])[C:23]([F:25])=[CH:24][C:19]=2[O:18][CH2:17][C:16]1=[O:26])#[N:13]

Participants

Conditions

Temperature: 0 °C

Procedure

98% nitric acid (0.71 g) was added dropwise to acetic anhydride (11.3 ml) at a temperature of 0° C. Subsequently a few drops of concentrated sulfuric acid were added thereto as catalyst, and the mixture was stirred for a while at 0° C. 4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (2.06 g) was added little by little thereto and stirred continuously at 0° C. for 30 minutes. A solution consisting of sodium hydride (10 g) and water (88 ml), cooled previously to 0° C., was added dropwise at 0° C. to neutralize the reaction liquor. The liquor was extracted with methylisobutyl ketone, and the extraction liquor was washed with water and a table salt solution, then dried with anhydrous sodium sulfate. The solvent was distilled off to give the desired 4-cyanomethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.39 g). mp. 204°-206° C.

Workup

stirringstirred continuously at 0° C. for 30 minutes
temperaturecooled previously to 0° C.
additionwas added dropwise at 0° C.
extractionThe liquor was extracted with methylisobutyl ketone
washthe extraction liquor was washed with water
dry with materiala table salt solution, then dried with anhydrous sodium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-1691690df9364171ab99679a653b8843
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04798620

Reaction notes

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