Water → HCID 68488610, compound

HRID 1878004Notes

Reaction equation

HRID 1878004 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH2:16][CH2:17][CH2:18][OH:19])([C:12]([F:15])([F:14])[F:13])[C:6]=2[CH:20]=1.O.CC([OH:25])C.[OH-].[Na+]>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH2:16][CH2:17][C:18]([OH:25])=[O:19])([C:12]([F:14])([F:15])[F:13])[C:6]=2[CH:20]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 68490016HCID 68490016, compound

Product 1

HCID 68488610HCID 68488610, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolventHCID 131709961Jones' reagentSolvent

Procedure

While stirring a solution of 6-chloro-4-(3-hydroxypropyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (1.0 g, 3.23 mmol) in acetone (20 mL), Jones reagent (8 N chromic acid, H2SO4—H2O solution, 2 mL) was added dropwise thereto at room temperature. Then water (20 mL) was added thereto and the solution was stirred at room temperature for 3 hours. Then, to the reaction solution, 2-propanol was added and the solution was stirred at room temperature for 5 minutes. After the reaction solution was diluted with ethyl acetate, a 8 N aqueous sodium hydroxide solution was added thereto, and the aqueous layer was separated. After the aqueous layer was acidified by adding 8 N hydrochloric acid thereto, the solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and saturated brine, and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure, whereby the objective compound (726 mg, 70%) was obtained as a pale yellow solid.

Workup

  1. additionwas added dropwise
  2. customat room temperature
  3. stirringthe solution was stirred at room temperature for 5 minutes
  4. customthe aqueous layer was separated
  5. additionby adding 8 N hydrochloric acid
  6. additionthe solution was diluted with ethyl acetate
  7. customthe organic layer was separated
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customAfter the drying agent was removed by filtration
  11. customthe solvent was evaporated under reduced pressure, whereby the objective compound (726 mg, 70%)
  12. customwas obtained as a pale yellow solid

Sources & evidence

ORD record
ord-603eaed7cca04cb59e6fd818aa5d3de4
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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