Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-hydroxy-5-methoxybenzoate

HRID 2102811

Reaction equation

HRID 2102811 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N+:21]([O-])=O)[CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[NH2:21][C:11]1[CH:10]=[C:9]([OH:8])[C:18]([O:19][CH3:20])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 22667033Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23132473Methyl 2-amino-4-hydroxy-5-methoxybenzoateYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 1 l Schlenk flask filled with argon, methyl 4benzyloxy-5-methoxy-2-nitrobenzoate (11.60 g, 36.6 mmol) and palladium on charcoal (1.17 g, 10% Pd, 1.1 mmol Pd) were combined and tetrahydrofuran (250 mL) was added. The argon was replaced with hydrogen (1 bar), and the mixture was vigorously stirred at r.t. until completion of the reaction. The palladium was separated by filtration through a pad of celite and the solvent was removed to obtain methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol, 98%) which was used without further purification LC/ESI-MS: m/z=166 [M−CH4O+H]+; Rt=2.17 min.

Workup

  1. customThe palladium was separated by filtration through a pad of celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-96f0e1d9de9b48f483c376647f0bb9b6
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Linked notes

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