Reaction #684962

ord-7f09f82c6daf47efaf0b14092852a6a1

Reaction equation

O=C[O-].[NH4+]
ammonium formate
COc1cccc(C(O)C[N+](=O)[O-])c1
compound
COc1cccc(C(O)C[N+](=O)[O-])c1
1-(3-Methoxyphenyl)-2-nitro-1-ethanol
COc1cccc(C(O)CN)c1
title compound
Yield 72.6%
COc1cccc(C(O)CN)c1
2-Amino-1-(3-methoxyphenyl)-1-ethanol
Yield 72.6%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe catalyst was removed by filtration
  2. 2
    workup.ADDITIONthe filtrate was diluted with ether
  3. 3
    Otherprecipitates
  4. 4
    Otherwere removed by filtration
  5. 5
    Concentrationthe obtained filtrate was concentrated

Procedure

Palladium-carbon (10%, 0.64 g) and ammonium formate (4.8 g) were added to a mixed solution of the compound of Example B142 (3.0 g, 15 mmol) in tetrahydrofuran (43 ml) and methanol (43 ml), and this mixture was stirred at room temperature for 18 hours. The catalyst was removed by filtration, the filtrate was diluted with ether, precipitates were removed by filtration, and the obtained filtrate was concentrated to give the title compound (1.82 g). This compound was used in the following reaction without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07897387B2uspto-grants-2011_03