Hydrochloric Acid → 4-Amino-5-chloro-2-methoxybenzoic acid

HRID 1390265Notes

Reaction equation

HRID 1390265 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13]C(=O)C)[C:10]([Cl:17])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH2:13])[C:10]([Cl:17])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77721Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Product 1

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

25.75 grs (0.1 mol) methyl 2-methoxy-4-acetamido-5-chlorobenzoate were introduced into a 500 ml flask, suspended in 100 ml ethanol. 40 grs NaOH, dissolved in 150 cc of water, were added and the mixture was heated under reflux for 2.5 hours. The mixture was diluted with water and made acid with concentrated HCl. The white solid which precipitated was collected and recrystallized from methanol. Weight: 17 grs m.p. = 213°-215° C. Yield = 84%.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2.5 hours
  4. customThe white solid which precipitated
  5. customwas collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a8f3e929233b43af832301d7bdb53824
Source dataset
uspto-grants-1979_02
Patent number
US04138492

Reaction notes

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