Acetic Anhydride → HCID 23358129, compound

HRID 233818Notes

Reaction equation

HRID 233818 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[C:15]=2[OH:18])[CH2:10]1.C([O-])(=O)C.[Na+]>O>[C:1]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[C:15]=2[OH:18])[CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 216088HCID 216088, compoundHCID 517045Sodium Acetate

Product 1

HCID 23358129HCID 23358129, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride is added to a mixture of 2-amino-4,5-dihydroxyindane [Cannon, J. G., et al., J. Med. Chem. 27, 922(1984)] in water containing sodium acetate. The mixture is chilled and stirred in ice for 4 hours followed by filtration to give N-acetyl-2-amino-4,5-dihydroxyindane. Benzylbromide, powdered potassium carbonate and acetone is added to the isolated N-acetyl-2-amino-4,5-dihydroxyindane and the mixture is stirred for 18 hours. The reaction mixture is poured into water, extracted and evaporated in vacuo to give N-acetyl-2-amino-4,5-dibenzyloxyindane. Hydrolysis with ethanolic sodium hydroxide gives 2-amino-4,5-dibenzyloxyindane.

Workup

  1. temperatureThe mixture is chilled
  2. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-64079bf8286b49f3aa93cb9d59bcff3b
Source dataset
uspto-grants-1997_01
Patent number
US05594027

Reaction notes

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