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

HRID 729425Notes

Reaction equation

HRID 729425 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

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 219793946,7-Difluoro-3-methyl-3,4-dihydro-5-oxa-2a-aza-acenaphthylene-1,2-dione

Product 1

HCID 219790297,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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

  1. filtrationThe reaction is filtered
  2. customto remove a trace of insoluble material
  3. customthe precipitate is removed by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e5f23e0b1a67497fb664e79fd962a808
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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