Hydrogen Peroxide → 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylic acid

HRID 10340Notes

Reaction equation

[F:1][C:2]1[C:12]([F:13])=[CH:11][C:10]2=[C:14]3[C:3]=1[O:4][CH2:5][CH:6]([CH3:17])[N:7]3C(=O)[C:9]2=[O:15].[OH:18]O>[OH-].[Na+]>[F:13][C:12]1[C:2]([F:1])=[C:3]2[O:4][CH2:5][CH:6]([CH3:17])[NH:7][C:14]2=[C:10]([C:9]([OH:15])=[O:18])[CH:11]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A suspension of 6.9 g (28.8 mmol) of 6,7-difluoro-3-methyl-3,4-dihydro-5-oxa-2a-aza-acenaphthylene-1,2-dione (Example 30) in 250 mL of 4.5% aqueous sodium hydroxide is treated dropwise with 16.4 mL of 30% hydrogen peroxide over 1 hour. The reaction is filtered to remove a trace of insoluble material and the filtrate is acidified to pH 4.5 with acetic acid. After cooling to 5° C., the precipitate is removed by filtration, washed with water and dried in vacuo to give 5.5 g of the title compound, mp 200–202° C.

Workup

filtrationThe reaction is filtered
customto remove a trace of insoluble material
customthe precipitate is removed by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-4fd926229a494c629b68840a11ffe7c1
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094780B1

Reaction notes

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