Methanol → Methyl 5-amino-o-anisate

HRID 71541

Reaction equation

HRID 71541 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:22]O>[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH3:22])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 24436Sodium SulfateHCID 87041Methyl 5-nitrosalicylate

Product 1

HCID 89843Methyl 5-amino-o-anisate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The hydrogenation of methyl 2-hydroxy-5-nitrobenzoate (700 mg, 3.3 mmol) using 10% Pd—C (100 mg) and Na2SO4 (100 mg) in MeOH at 50 psi gave methyl 5-amino-2-methoxybenzoate (600 mg).

Sources & evidence

ORD record
ord-08efbd127163432e91321c6abd1742e6
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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