1-(3,4-Dihydroxy-2-methoxyphenyl)-2-(1,1-dimethylpropylamino)ethanone → 4-[2-(1,1-Dimethylpropylamino)-1-hydroxyethyl]-3-methoxybenzene-1,2-diol

HRID 966096Notes

Reaction equation

HRID 966096 reaction equation
[OH:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([C:9](=[O:17])[CH2:10][NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])[CH:5]=[CH:6][C:7]=1[OH:8]>[Pt]=O.CO>[CH3:16][C:12]([NH:11][CH2:10][CH:9]([C:4]1[C:3]([O:18][CH3:19])=[C:2]([OH:1])[C:7]([OH:8])=[CH:6][CH:5]=1)[OH:17])([CH3:15])[CH2:13][CH3:14]

Participants

4

Reactant 1

HCID 223145401-(3,4-Dihydroxy-2-methoxyphenyl)-2-(1,1-dimethylpropylamino)ethanone

Product 1

HCID 98168584-[2-(1,1-Dimethylpropylamino)-1-hydroxyethyl]-3-methoxybenzene-1,2-diol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

6.5 g of 1-(3,4-dihydroxy-2-methoxyphenyl)-2-(1,1-dimethylpropylamino)ethanone are hydrogenated with 0.1 g of platinum oxide as catalyst in 125 mL of methanol. The catalyst is suction filtered and the solvent is distilled off under reduced pressure. The residue is dissolved in ethyl acetate, the precipitated crystals are suction filtered and washed with ethyl acetate and diethyl ether. Yield: 5.5 g (85%; benzoate); melting point: 172° C.-174° C.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. filtrationfiltered
  5. washwashed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-01686959d43443dd92dfca8b55abfffa
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

Loading…