4-Acetamido-2-hydroxy-5-nitrobenzoic acid → 4-Amino-2-hydroxy-5-nitrobenzoic acid

HRID 2205117Notes

Reaction equation

HRID 2205117 reaction equation
C([NH:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([OH:17])[CH:6]=1)(=O)C>Cl>[NH2:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([OH:17])[CH:6]=1

Participants

3

Reactant 1

HCID 672874384-Acetamido-2-hydroxy-5-nitrobenzoic acid

Product 1

HCID 218421914-Amino-2-hydroxy-5-nitrobenzoic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-acetamido-2-hydroxy-5-nitrobenzoic acid (5 g, 20.8 mmol, 1.00 equiv) and HCl (aq.) (110 mL, 6N) in a 500-mL round-bottom flask was allowed to react, with stifling, for 2 hrs while the temperature was maintained at reflux. The mixture was cooled. The solids were collected by filtration, yielding 3.4 g (82%) of 4-amino-2-hydroxy-5-nitrobenzoic acid as a brown solid.

Workup

  1. customto react
  2. temperaturewas maintained
  3. temperatureat reflux
  4. temperatureThe mixture was cooled
  5. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-68bb80ab28f04793bc107359e15c65fb
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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