Methanol → 5-Amino-2,3-dimethylbenzoic acid

HRID 343538Notes

Reaction equation

HRID 343538 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[CH3:15]O>[Pd]>[CH3:15][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[C:9]([NH2:12])[CH:10]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 4377758Methyl 2-methyl-5-nitrobenzoate

Product 1

HCID 184645405-Amino-2,3-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Combine methyl 2-methyl-5-nitrobenzoate (5.32 g, 27.2 mmol) and methanol (100 mL). Add 5% palladium-on-carbon (0.27 g). Hydrogenate on a pressure apparatus at 50 psi. After 18 hours, filter through celite to remove the catalyst and evaporate the filtrate in vacuo to give methyl 2-methyl-5-aminobenzoic acid: Rf =0.34 (silica gel, ethyl acetate/hexane 1/4).

Workup

  1. filtrationfilter through celite
  2. customto remove the catalyst
  3. customevaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-f6f387702faa45c984dc1916f4057b41
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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