HCID 15528422, compound → 2-Amino-1-(3-methoxyphenyl)ethanol

HRID 1685299Notes

Reaction equation

HRID 1685299 reaction equation
[N+:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[OH:6])([O-])=O>CO.O=[Pt]=O>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[OH:6]

Participants

4

Reactant 1

HCID 15528422HCID 15528422, compound

Product 1

HCID 5866792-Amino-1-(3-methoxyphenyl)ethanolYield 29%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-nitro-1-(3-methoxyphenyl)ethanol (688 mg, 3.49 mmol), PtO2 (160 mg) in MeOH (10 mL) was pressurized to 40 psi H2 and shaken in a Parr shaker overnight. The reaction was depressurized, filtered through Celite, concentrated, purified by flash chromatography (0-100% EtOAc:hexane) to afford 169 mg of the product as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.24 (t, J=7.96 Hz, 1H), 6.85-6.93 (m, 2H), 6.80 (m, 1H), 4.60 (dd, J=7.83, 4.04 Hz, 1H), 3.79 (s, 3H), 2.96 (dd, J=12.76, 3.92 Hz, 1H), 2.79 (dd, J=12.76, 7.71 Hz, 1H), 2.19 (s, 3H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. custompurified by flash chromatography (0-100% EtOAc:hexane)

Sources & evidence

ORD record
ord-5d88bd0067da45e0ae237fa8b73a2dd4
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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