Sodium Hydroxide → HCID 15078415, compound

HRID 1110441Notes

Reaction equation

HRID 1110441 reaction equation
[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14]C(=O)CCl)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:14])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15078414HCID 15078414, compound

Product 1

HCID 15078415HCID 15078415, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.5 g of 2-acetylamino-5-chloroacetoxyindan, 50 ml of methanol and 46 ml of an aqueous 1N sodium hydroxide solution is stirred at room temperature for 2.5 hours. The reaction mixture is evaporated to remove methanol and the residual aqueous layer is washed with dimethyl ether, acidified and extracted with ethyl acetate. The extract is washed successively with an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography and recrystallized from isopropanol-isopropyl ether to give 1.01 g of 2-acetylamino-5-hydroxyindan as colorless needles. Yield: 61%

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove methanol
  3. washthe residual aqueous layer is washed with dimethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed successively with an aqueous sodium bicarbonate solution
  6. dry with materialan aqueous sodium chloride solution, dried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography
  10. customrecrystallized from isopropanol-isopropyl ether

Sources & evidence

ORD record
ord-0adf52c66b78459a80487acbb88f08af
Source dataset
uspto-grants-1990_12
Patent number
US04975460

Reaction notes

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