Sodium Hydroxide → HCID 15453740, compound

HRID 1108218Notes

Reaction equation

HRID 1108218 reaction equation
O1CCOCC1.[C:7]([NH:15][C:16]1[C:17]([N+:30]([O-:32])=[O:31])=[CH:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22](Br)[CH:21]([OH:28])[C:20]=2[CH:29]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O>[C:7]([NH:15][C:16]1[C:17]([N+:30]([O-:32])=[O:31])=[CH:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]3[O:28][CH:21]3[C:20]=2[CH:29]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18784527HCID 18784527, compound

Product 1

HCID 15453740HCID 15453740, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixed solution of a 1,4-dioxane (5 mL) and water (2.5 mL) in which a 6-(benzoylamino)-3-bromo-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran-4-ol (III-1) (223 mg, 0.53 mmol) was dissolved was added with a sodium hydroxide (25.5 mg, 1.2 eq.) and stirred at room temperature for one hour. After the solution was diluted with water, the resulting mixture was extracted with an ethyl acetate and the organic layer was washed with an aqueous saturated sodium chloride solution, the layer was dried over a sodium sulfate anhydride. After the solvent was distilled off, the obtained residue was purified through silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the intended product (147 mg, 81%) as a yellow solid.

Workup

  1. extractionthe resulting mixture was extracted with an ethyl acetate
  2. washthe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialthe layer was dried over a sodium sulfate anhydride
  4. distillationAfter the solvent was distilled off
  5. customthe obtained residue was purified through silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-452c58663e584c9b8f74be1ac5f28864
Source dataset
uspto-grants-2000_05
Patent number
US06066631

Reaction notes

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