Tetrahydrofuran → Methyl p-aminosalicylate

HRID 1793634Notes

Reaction equation

HRID 1793634 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[OH:13].C1COCC1>CCO.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[OH:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 139539Salicylic acid, 4-nitro-, methyl ester

Product 1

HCID 77787Methyl p-aminosalicylateYield 101.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

2-Hydroxy-4-nitro-benzoic acid methyl ester (14 g) was dissolved in EtOH (100 ml) and THF (10 ml) and stirred under hydrogen (1 atm) in the presence of PtO2 for 24 h. The reaction mixture was then filtered through a celite bed. The filtrate was concentrated to give 12 g of 4-Amino-2-hydroxy-benzoic acid methyl ester as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite bed
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1b45bffd7f014cd48f64d60f2efc62db
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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