Dichloromethane → 1-(3-Amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone

HRID 1662954Notes

Reaction equation

HRID 1662954 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N+:19]([O-])=O)[C:12]([OH:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl>CO.[Rh]>[NH2:19][C:11]1[C:12]([OH:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 210728231-(5-(Benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

Product 1

HCID 210728221-(3-Amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

69.5 g (242 mmol) 1-(5-benzyloxy-2-hydroxy-3-nitrophenyl)-ethanone are dissolved in 1.4 L methanol and hydrogenated in the presence of 14 g rhodium on charcoal (10%) as catalyst at 3 bar and ambient temperature. Then the catalyst is filtered off and the filtrate is evaporated down. The residue is reacted further without additional purification. Yield: 60.0 g (96%), Rf value=0.45 (dichloromethane on silica gel).

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe filtrate is evaporated down
  3. customThe residue is reacted further without additional purification

Sources & evidence

ORD record
ord-b31a6aac60bb4ed08bc8daa8762d43f0
Source dataset
uspto-grants-2011_10
Patent number
US08034809B2

Reaction notes

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