Methanol → Methyl 4-amino-5-chloro-2-hydroxybenzoate

HRID 973412Notes

Reaction equation

HRID 973412 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:9][C:10]=1[Cl:11])[C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:9][C:10]=1[Cl:11])[C:6]([O:8][CH3:17])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 148832224-Amino-5-chloro-2-hydroxybenzoic acid

Product 1

HCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoate

Conditions

Temperature
0 °C

Procedure

4-Amino-5-chlorosalicylic acid (24 g) is added to a stirred solution of thionyl chloride (30 ml) in methanol (300 ml) cooled to 0° C., and the mixture is stirred under reflux for 18 hours. The reaction mixture is evaporated and the residue is recrystallized from EtOH-H2O to give methyl 4-amino-5-chlorosalicylate which is used directly in the next step.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is recrystallized from EtOH-H2O

Sources & evidence

ORD record
ord-95dbf6147f4842b68bb42b79d713667b
Source dataset
uspto-grants-1991_11
Patent number
US05063230

Reaction notes

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