Ammonium formate → Ethyl 3-amino-2-hydroxybenzoate

HRID 912424Notes

Reaction equation

HRID 912424 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[OH:14])[CH3:2].[H][H].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[OH:14])[CH3:2]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 12157235Ethyl 2-hydroxy-3-nitrobenzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22096614Ethyl 3-amino-2-hydroxybenzoateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-hydroxy-3-nitrobenzoic acid ethyl ester 8.4 g (40 mmol) of step 1 in methanol 100 mL was added 5% Pd/C 0.84 g, after which the reactor was filled hydrogen gas, followed by stirring at room temperature for 5 hrs. Ammoniumformate 0.5 g was added to the reaction mixture before re-filling with hydrogen gas and re-stirring at room temperature for 24 hrs. The catalyst was removed by celite filtration, followed by vacuum concentration to afford the title compound 7.2 g (yield 99%).

Workup

  1. stirringre-stirring at room temperature for 24 hrs
  2. customThe catalyst was removed by celite filtration
  3. concentrationfollowed by vacuum concentration

Sources & evidence

ORD record
ord-b8fdd6f131f24842af3a96005482d925
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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