Methanol → Methyl p-aminosalicylate

HRID 1932163Notes

Reaction equation

HRID 1932163 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-6e2d7af7fdea4f91b98ff3f13734e2d8
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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