Ammonium Hydroxide → t-Butyl [3-(aminomethyl)phenoxy]acetate

HRID 23788Notes

Reaction equation

HRID 23788 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[N:16]O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+]>CCO.[Ni]>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 73704862(3-(Hydroxyimino-methyl)-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent3×

Procedure

To a solution of [3-(hydroxyimino-methyl)-phenoxy]-acetic acid tert-butyl ester (2.25 g, 5.96 mmol) in EtOH (10 mL) was added Raney Nickel (about 1 g, washed with water followed by EtOH) in 100 mL ethanol. Additional EtOH (90 mL) was required for the transfer. Ammonium hydroxide (10 mL) was added and the mixture was shaken under 45 psi of H2 for 4 hours. The catalyst was removed via filtration through Celite® (diatomaceous earth) and the solution was concentrated to a clear oil. Purification via flash chromatography on silica gel (96.5/3.5/0.1 to 9/1/0.1 CH2Cl2/MeOH/NH4OH) afforded the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.23 (m, 1H), 6.92 (m, 2H), 6.72 (d, 1H), 4.50 (s, 2H), 3.82 (s, 2H), 1.96 (m, 2H), 1.46 (s, 9H); MS 238 (M+1).

Workup

  1. customThe catalyst was removed via filtration through Celite® (diatomaceous earth)
  2. concentrationthe solution was concentrated to a clear oil
  3. customPurification via flash chromatography on silica gel (96.5/3.5/0.1 to 9/1/0.1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-24f1a702e5c44e9e9a53d69639979f8c
Source dataset
uspto-grants-2005_02
Patent number
US06852863B2

Reaction notes

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