Hydrochloric Acid → 4-Amino-2-methoxy-5-nitrobenzoic acid

HRID 1410235Notes

Reaction equation

HRID 1410235 reaction equation
C([NH:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([O:19][CH3:20])[CH:6]=1)(=O)C.[OH-].[Na+].O.Cl>CCO>[NH2:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:19][CH3:20])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59529886Ethyl 4-acetamido-2-methoxy-5-nitrobenzoate

Product 1

HCID 1010164-Amino-2-methoxy-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-acetamido-2-methoxy-5-nitrobenzoate (4.0 g; 14.9 mmol) and NaOH (40 mL, 1 M aq; 40 mmol) in EtOH (80 mL) was refluxed for 2 h. The mixture was cooled to rt and water (20 mL) was added. The mixture was acidified by HCl (6 M aq) and the sub-title compound was filtered off. Yield: 3.0 g (95%).

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationthe sub-title compound was filtered off

Sources & evidence

ORD record
ord-78d52116acee451fa6b339bac10287d6
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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