Methyl 2-hydroxy-3-nitrobenzoate → Methyl 3-amino-2-hydroxybenzoate

HRID 1470613Notes

Reaction equation

HRID 1470613 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H][H]>CO.[Pd]>[NH2:12][C:11]1[C:2]([OH:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 596904Methyl 2-hydroxy-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 2-hydroxy-3-nitrobenzoate (2 g, 0.010 mol) in methanol (30 mL), was hydrogenated with a hydrogen balloon in the presence of 10% palladium on chacoal (600 mg) for 7 h. After the reaction is completed, the reaction mixture was filtered through celite bed and the filtrate was concentrated under reduced pressure to obtain 1.6 g of the above required compound (72%) as a grey coloured solid.

Workup

  1. filtrationthe reaction mixture was filtered through celite bed
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1cadf9fb22c34dc0a68c6d54891aa2ed
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

Loading…