Hydrochloric Acid → N-(3-Amino-4-methoxyphenethyl)acetamide hydrochloride

HRID 551600Notes

Reaction equation

HRID 551600 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:5][C:4]=1[N+:15]([O-])=O.[ClH:18]>C(O)C.[Pd]>[ClH:18].[NH2:15][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15491289N-(4-Methoxy-3-nitrophenethyl)acetamide

Product 1

HCID 45074592N-(3-Amino-4-methoxyphenethyl)acetamide hydrochlorideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-(4-methoxy-3-nitrophenyl)ethyl]acetamide (7.4 g) in 150 mL of ethanol was hydrogenated in the presence of 3.5 mL of concentrated HCl and 0.4 g of 10% Pd/C at 30-40 psi for 3 hours in a Parr shaker. After this time, the catalyst was filtered off, and the solvent was removed by rotary evaporation to yield 7.1 g of N-[-2-(3-amino-4-methoxyphenyl)ethyl]acetamide hydrochloride as an off-white solid (94.0% yield). 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

Workup

  1. filtrationAfter this time, the catalyst was filtered off
  2. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-bd30d2086dab4740822088470f8b6ef8
Source dataset
uspto-grants-2011_05
Patent number
US07947761B2

Reaction notes

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