Methanol → 1-[3-Amino-4-(benzyloxy)phenyl]ethan-1-one

HRID 1955784Notes

Reaction equation

HRID 1955784 reaction equation
CO.[C:3]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=2[N+:20]([O-])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O=[Pt]=O.CC(O)C>[C:3]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=2[NH2:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanone

Product 1

HCID 155794401-[3-Amino-4-(benzyloxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 3776IsopropanolSolvent

Procedure

A mechanically stirred MeOH (3.8 L) suspension containing 1-[4-phenylmethoxy-3-nitrophenyl]ethanone (76.5 g, 282 mmol) was degassed with argon for 40 minutes at ~10° C. prior to addition of PtO2 (2.34 g, 10 mmol). Hydrogen was sparged into the reaction mixture at 8°-10° C. via a subsurface gas inlet. After eight hours, the completed reaction was degassed with Ar while being warmed to ~15° C., diluted with CHCl3 (250 mL) and filtered. The filtrate was stripped to give 70 g crude product which, after trituration for ten minutes with i-PrOH (450 mL) at 60° C., yielded 57.4 (84%) of the title compound.

Workup

  1. customwas degassed with argon for 40 minutes at ~10° C.
  2. customHydrogen was sparged into the reaction mixture at 8°-10° C. via a subsurface gas inlet
  3. customthe completed reaction
  4. customwas degassed with Ar
  5. temperaturewhile being warmed to ~15° C.
  6. additiondiluted with CHCl3 (250 mL)
  7. filtrationfiltered
  8. customto give 70 g crude product which

Sources & evidence

ORD record
ord-7f2284044fa5460ea743e5fb39b4a190
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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