Methanol → Methyl p-aminosalicylate

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

Reactant 2

HCID 887Methanol

HCID 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

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

Sources & evidence

ORD record: ord-aba6bdb960ce41dead32062ee1bf5d05
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822685B2

Reaction notes

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