Methanol → Methyl p-aminosalicylate

HRID 603778Notes

Reaction equation

HRID 603778 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-9d7fa5a3c10e468e841be0f7e782038f
Source dataset
uspto-grants-2011_03
Patent number
US07906644B2

Reaction notes

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