Hydrochloric Acid → 7,8-Difluoro-4h-benzo[1,4]oxazine-3-one-6-carboxylic acid

HRID 495444Notes

Reaction equation

HRID 495444 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:14]([C:15]([O:17]C)=[O:16])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[C:5]=1[F:19].Cl>C1COCC1>[F:3][C:4]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[C:5]=1[F:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 223266717,8-Difluoro-6-methoxycarbonyl-4H-benzo[1,4]oxazine-3-one

Product 1

HCID 223266397,8-Difluoro-4h-benzo[1,4]oxazine-3-one-6-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2M solution of aqueous sodium hydroxide (30 mL) was added to a suspension of 7,8-difluoro-6-methoxycarbonyl-4H-benzo[1,4]oxazine-3-one (4.8 g, 19.88 mmoL) in THF (100 mL). The mixture was allowed to stir for 3 hours and the total volume was then reduced in vacuo to half. It was treated with 2M hydrochloric acid to caused a solid precipitate which was filtered, washed with water three times and then dried in vacuo to give the title compound (3.6 g, 80%).

Workup

  1. filtrationwas filtered
  2. washwashed with water three times
  3. customdried in vacuo

Sources & evidence

ORD record
ord-58a3446a708e42d78c9fc3e997e7f675
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

Loading…