Hydrochloric Acid → 4-Amino-5-cyano-2-hydroxybenzoic acid

HRID 249969Notes

Reaction equation

HRID 249969 reaction equation
[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[C:4]([OH:15])[CH:3]=1.[OH-].[Na+].Cl>O>[NH2:1][C:2]1[C:12]([C:13]#[N:14])=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:15])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3018374Ethyl 4-amino-5-cyano-2-hydroxybenzoate

Product 1

HCID 125651974-Amino-5-cyano-2-hydroxybenzoic acidYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-amino-5-cyano-2-hydroxybenzoate (3 g, 14.55 mmol) is treated with 60 ml of a 10% strength sodium hydroxide solution and the mixture is stirred at 50° C. for one hour. After cooling, the reaction solution is acidified with concentrated hydrochloric acid, diluted with water and the precipitate is filtered off with suction. The desired product is obtained after recrystallization from ethanol in 62% yield (1.6 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-5010a193e6f04b1990b5337828cc718c
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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