Sodium Hydroxide → 4-Amino-3-chlorobenzoic acid

HRID 1717280Notes

Reaction equation

HRID 1717280 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[Cl:12].[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Product 1

HCID 172114-Amino-3-chlorobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 4-amino-3-chlorobenzoate (3.3 g) in ethanol (53 ml) was added 8N aqueous sodium hydroxide solution (4.4 ml), and the mixture was stirred at 40° C. for 3.5 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in water. The obtained aqueous solution was washed with diethyl ether and neutralized with 1N aqueous hydrochloric acid solution. The precipitated insoluble material was collected by filtration and air-dried to give the title compound as a pale-brown powder (3.0 g, 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washThe obtained aqueous solution was washed with diethyl ether and neutralized with 1N aqueous hydrochloric acid solution
  4. filtrationThe precipitated insoluble material was collected by filtration
  5. customair-dried

Sources & evidence

ORD record
ord-6f118fcc64a74a5b98aa6246ee726e86
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…