Methanol → Methyl p-aminosalicylate

HRID 1475004Notes

Reaction equation

HRID 1475004 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-a6527e57b6624065904892ed34d75800
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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