Sodium Hydroxide → HCID 59233312, compound

HRID 383907Notes

Reaction equation

HRID 383907 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]4[CH:19]=[CH:18][O:17][C:16]=24)[NH:13][C:12]([CH3:21])([CH3:20])[C:11](=[O:22])[C:10]3([CH3:24])[CH3:23])=[C:5]([CH3:25])[O:4][N:3]=1.[BrH:26].[NH+]1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[Br:26][C:18]1[O:17][C:16]2=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:25])[CH:8]=[C:9]3[C:14]([NH:13][C:12]([CH3:20])([CH3:21])[C:11](=[O:22])[C:10]3([CH3:24])[CH3:23])=[C:15]2[CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226041Pyridinium hydrobromideHCID 68558499HCID 68558499, compound

Product 1

HCID 59233312HCID 59233312, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-1,2,3,4-tetrahydro-furo[2,3-h]quinolin-3-one (31 mg) obtained in Example 93, 3) in THF (1.0 ml) was added pyridinium hydrobromide perbromide (29 mg) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was neutralized with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=3:2) to give the title compound (17 mg, 44%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=3:2)

Sources & evidence

ORD record
ord-897eccad0f6540c88169f23becfa6698
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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