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

HRID 1157445Notes

Reaction equation

HRID 1157445 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([N+:13]([O-])=O)=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6]>CO.[Pd]>[NH2:13][C:8]1[CH:9]=[C:10]([O:11][CH3:12])[C:2]([OH:1])=[CH:3][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

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

Product 1

HCID 198070282-Amino-5-hydroxy-4-methoxybenzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-hydroxy-4-methoxy-6-nitrobenzoic acid (Journal of Natural Product, 1986, 49 (3), 445-448) (10.0 g, 46.9 mmol) in methanol (150 mL) was added 10% Pd/C (0.1 eq.). The reaction was stirred under a hydrogen atmosphere (1 atm.) at room temperature for 5 h. The solution was filtered and the filtrate was evaporated to afford 2-amino-5-hydroxy-4-methoxybenzoic acid (INTERMEDIATE V1.1) (7.0 g, 38.3 mmol, 82%).

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ced9202b5b3d4732b5dd2a371d664640
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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