Sodium Hydroxide → 2-Methoxy-4-(methylamino)-5-nitrobenzoic acid

HRID 1410220Notes

Reaction equation

HRID 1410220 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:13](C)[C:14](=O)C)[C:10]([N+:18]([O-:20])=[O:19])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][CH3:14])[C:10]([N+:18]([O-:20])=[O:19])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10379023Methyl 2-methoxy-4-(N-methylacetamido)-5-nitrobenzoate

Product 1

HCID 109879372-Methoxy-4-(methylamino)-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-methoxy-4-(N-methylacetamido)-5-nitrobenzoate (2.1 g; 0.74 mmol), aqueous NaOH (29 mL; 1 M; 29 mmol) and EtOH (30 mL) was refluxed for 2 h. The mixture was thereafter concentrated and the remaining aqueous phase was acidified to strongly acidic pH with acetic acid, sonicated and filtered to give the sub-title compound.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationThe mixture was thereafter concentrated
  3. customsonicated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-70040ff55c404bd998431a18ee25facc
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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