Acetic Anhydride → N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 340664Notes

Reaction equation

HRID 340664 reaction equation
Br.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:13])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(=O)([O-])O.[Na+]>O1CCCC1>[OH:12][C:11]1[C:3]([NH:2][C:21](=[O:23])[CH3:22])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:13])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 673534616-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide

Product 1

HCID 67354064N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)acetamideYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Amino-7-hydroxyindan-1-one hydrobromide (800 mg, 3.28 mmol) was suspended in tetrahydrofuran (20 mL), triethylamine (571 μL, 4.10 mmol) and acetic anhydride (387 μL, 4.10 mmol) were added, and the mixture was stirred at room temperature for 1.5 hr. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=60/40→100/0) to give the title compound (481 mg, yield 71%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=60/40→100/0)

Sources & evidence

ORD record
ord-96d5185c89414d9b81ddcb92b71679c3
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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