Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate → Methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoate

HRID 2189239Notes

Reaction equation

HRID 2189239 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:18]([O-])=O)[CH:4]=1.[H][H]>CO.O=[Pt]=O>[NH2:18][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 58394383Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58394329Methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoateYield 83%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate (3.39 g, 11.88 mmol) in methanol (40 mL) was hydrogenated at 50 psi hydrogen gas in the presence of PtO2 (0.050 g) using a Parr hydrogenator for 24 h. The reaction mixture was filtered and concentrated to give the title compound as an oil (2.51 g, 83%).

Workup

  1. customfor 24 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6851edb6cc3a454292388562144440ee
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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