Ammonium Chloride → 2-Amino-4-methoxy-5-(2-methoxyethoxy)benzamide

HRID 1407013Notes

Reaction equation

HRID 1407013 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:17]([O-])=O)[CH:4]=1.[NH4+].[Cl-]>COCCOC.CO.[Pd]>[NH2:17][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 593618834-Methoxy-5-(2-methoxyethoxy)-2-nitrobenzamide

Product 1

HCID 593619522-Amino-4-methoxy-5-(2-methoxyethoxy)benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzamide (4.5 g, contains some NH4Cl) and 10% Pd/C (ca. 0.5 g) in DME (200 mL) and MeOH (200 mL) was hydrogenated under a balloon of H2 at RT for 12 h. The mixture was filtered through a pad of Celite® and concentrated in vacuo to give 2-amino-4-methoxy-5-(2-methoxyethoxy)benzamide as an off white solid (2.8 g, 11.6 mmol). HPLC retention time 2.80 mins.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-913498b9905e4b64a8d0d4341cb29da1
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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