N-[2-Hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide → N-[1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]acetamide

HRID 481272Notes

Reaction equation

HRID 481272 reaction equation
[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH:3]([NH:6][C:7](=[O:9])[CH3:8])[CH2:4][OH:5]>CO>[OH:1][CH:2]([C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[CH:3]([NH:6][C:7](=[O:9])[CH3:8])[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 4335N-[2-Hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide

Product 1

HCID 287222N-[1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a clean, round bottom flask N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl] acetamide (1.27 g 5 mmoles) was dissolved in methanol (50 ml). The flask was then fitted with a suitable adaptor and coupled to an hydrogenation apparatus. The atmosphere in the flask was then replaced with nitrogen. The adaptor was then removed and 10% palladium on carbon catalyst (466 mg) was added to the flask. The adaptor was replaced and the hydrogenation apparatus manipulated to replace the atmosphere in the flask with hydrogen. The flask contents were then stirred at room temperature under an atmosphere of hydrogen overnight. The hydrogenation apparatus was manipulated to replace the atmosphere in the flask with nitrogen. The flask was then disconnected from the hydrogenation apparatus.

Workup

  1. customThe flask was then fitted with a suitable adaptor
  2. customThe adaptor was then removed
  3. addition10% palladium on carbon catalyst (466 mg) was added to the flask

Sources & evidence

ORD record
ord-51cf1a137cd74d9c9af50a2beb5d6f15
Source dataset
uspto-grants-1998_08
Patent number
US05789179

Reaction notes

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