Hydrochloric Acid → HCID 20071519, compound

HRID 981289Notes

Reaction equation

HRID 981289 reaction equation
[CH:1]1([C:4]2[C:5]([F:24])=[CH:6][C:7]3[C:17](=[O:18])[C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][N:9]4[CH:10]([CH3:14])[CH2:11][O:12][C:13]=2[C:8]=34)[CH2:3][CH2:2]1.[OH-].[Na+].C(O)C.Cl>C(OCC)(=O)C.O.O1CCOCC1>[CH:1]1([C:4]2[C:5]([F:24])=[CH:6][C:7]3[C:17](=[O:18])[C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:9]4[CH:10]([CH3:14])[CH2:11][O:12][C:13]=2[C:8]=34)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 20071531HCID 20071531, compound

Product 1

HCID 20071519HCID 20071519, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To 250 mg of ethyl 10-cyclopropyl-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylate were added 2.5 ml of a 1N aqueous sodium hydroxide solution, 2.5 ml of ethanol and 2.5 ml of dioxane in this order. The resulting mixture was stirred at room temperature for 1.5 hours. To the reaction mixture were added 10 ml of water and 20 ml of ethyl acetate in this order. The resulting mixture was adjusted to pH 3 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. Diethyl ether was added to the residue obtained and the resulting crystals were collected by filtration to obtain 200 mg (yield: 87.3%) of 10-cyclopropyl-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. customobtained
  7. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-cc88c4851502408291b43306ad01ae6e
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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