Methanol → Methyl p-aminosalicylate

HRID 1686731Notes

Reaction equation

HRID 1686731 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[CH3:12]O>>[OH:11][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:12])=[O:7])[NH2:1]

Participants

3

Reactant 2

HCID 887MethanolHCID 46494-Aminosalicylic Acid

Product 1

HCID 77787Methyl p-aminosalicylate

Procedure

A solution of 4-amino-2-hydroxybenzoic acid (1 g, 6.5 mmol) in MeOH (15 mL) and concentrated sulfonic acid (1 mL) was refluxed overnight. The reaction mixture was quenched with NaHCO3 aqueous solution (60 mL) and EtOAc (60 mL). The organic layer was separated, dried, evaporated to give 3-hydroxy-4-methoxycarbonylaniline.

Workup

  1. customThe reaction mixture was quenched with NaHCO3 aqueous solution (60 mL) and EtOAc (60 mL)
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-04709f98a2f1432ea9935ee1cb459153
Source dataset
uspto-grants-2012_04
Patent number
US08148525B2

Reaction notes

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