Ethyl 2-amino-5-chloro-3-hydroxybenzoate → 2-Amino-5-chloro-3-hydroxybenzoic acid

HRID 219438Notes

Reaction equation

HRID 219438 reaction equation
[NH2:1][C:2]1[C:12]([OH:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5]>Cl>[NH2:1][C:2]1[C:12]([OH:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Conditions

Temperature
80 °C

Procedure

Ethyl 2-amino-5-chloro-3-hydroxybenzoate (3.23 g) was dissolved in 160 ml of a 3N aqueous solution of hydrochloric acid and stirred at 85° C. for 3 hours and at 80° C. for 5 days. The reaction solution was cooled to room temperature, insoluble matters were filtered off, 320 ml of a 1N aqueous solution of sodium hydroxide was added to the filtrate and the mixture was stirred at room temperature for 1 hour. The resulting precipitate was filtered, washed with pure water and dried in vacuo to give 1.55 g of 2-amino-5-chloro-3-hydroxybenzoic acid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationinsoluble matters were filtered off
  3. addition320 ml of a 1N aqueous solution of sodium hydroxide was added to the filtrate
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with pure water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-25955cfa283840378b7e0e23c3b31448
Source dataset
uspto-grants-2012_06
Patent number
USRE043481E1

Reaction notes

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