Methanol → 4-amino-2,3-dihydro-1H-inden-2-ol

HRID 536446

Reaction equation

HRID 536446 reaction equation
C([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:14])[CH2:6]1)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[NH2:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH:5]([OH:4])[CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 132395844-amino-2,3-dihydro-1H-inden-2-yl acetate

Product 1

HCID 545954264-amino-2,3-dihydro-1H-inden-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A slurry of 4-amino-2,3-dihydro-1H-inden-2-yl acetate (12.6 g, 65.9 mmol; prepared according to US2003109700), MeOH (63 mL), and potassium carbonate (13.7 g, 99.0 mmol) was stirred at ambient temperature for 15 minutes. The reaction mixture was diluted with IPA (630 mL), passed through a plug of silica gel, washed with IPA (100 mL), and concentrated to give the title compound (9.70 g, 65.0 mmol, 99%). MS (DCI) m/z 267 (M+NH4)+.

Workup

  1. washwashed with IPA (100 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-228c365d383e4ceba0442cb320284762
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Linked notes

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