1-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-one → 1-(2-Amino-5-hydroxyphenyl)-2-methyl-1-propanone

HRID 396128Notes

Reaction equation

HRID 396128 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:20]([O-])=O)=[C:13]([C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])[CH:14]=1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:20][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][C:13]=1[C:15](=[O:19])[CH:16]([CH3:17])[CH3:18]

Participants

4

Reactant 1

HCID 230030601-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-one

Product 1

HCID 230030871-(2-Amino-5-hydroxyphenyl)-2-methyl-1-propanoneYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.2 g of palladium/carbon (10%) is suspended in a solution of 1.34 g (4.51 mmol) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-one in 50 ml of ethanol. The mixture is shaken under a hydrogen atmosphere at 3 bar for 4.5 h, then the mixture is filtered off through kieselguhr, the filtrate is concentrated in vacuo and the residue is purified on silica gel (cyclohexane/ethyl acetate 5:2-1:1). 511 mg (63%) of 1-(2-amino-5-hydroxyphenyl)-2-methyl-1-propanone are obtained.

Workup

  1. filtrationthe mixture is filtered off through kieselguhr
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe residue is purified on silica gel (cyclohexane/ethyl acetate 5:2-1:1)

Sources & evidence

ORD record
ord-170ae0dc62884323981a076ca699acae
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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