5-Hydroxy-4-methoxy-2-nitrobenzoic acid → 2-Amino-5-hydroxy-4-methoxybenzoic acid

HRID 415015Notes

Reaction equation

HRID 415015 reaction equation
[OH:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>CO.O=[Pt]=O>[NH2:11][C:5]1[CH:4]=[C:3]([O:14][CH3:15])[C:2]([OH:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 139156695-Hydroxy-4-methoxy-2-nitrobenzoic acid

Product 1

HCID 198070282-Amino-5-hydroxy-4-methoxybenzoic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

5-Hydroxy-4-methoxy-2-nitro-benzoic acid (18 g, 84.51 mmol, J Indian Chem. Soc. 1970, 70, 925) is suspended in MeOH (1 L) and treated PtO2 (100 mg). The flask is flushed with hydrogen gas and the reaction mixture is stirred under hydrogen atmosphere (45 psi) for 4 hours. The reaction mixture is filtered through a celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MgSO4) and concentrated to yield 15.06 g (82.3 mmol, 97%) of the desired product.

Workup

  1. customThe flask is flushed with hydrogen gas
  2. filtrationThe reaction mixture is filtered through a celite plug
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe crude product is redissolved in DCM
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61f61483f5ca48feb842aa388874f492
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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