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

HRID 1403586Notes

Reaction equation

HRID 1403586 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10]([N+:23]([O-])=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[NH2:23][C:10]1[C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 70665192Methyl 2-methoxy-4-(4-methoxybenzylamino)-5-nitrobenzoate

Product 1

HCID 70664744Methyl 5-amino-2-methoxy-4-(4-methoxybenzylamino)benzoateYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-methoxy-4-(4-methoxybenzylamino)-5-nitrobenzoate (544 g, 144.37 mmol) in methanol (1500 mL) was added palladium on carbon (15 g). The solution was allowed to react for 2 h at room temperature under an atmosphere of H2 (g). The solids were filtered from the resulting solution, and the filtrate was concentrated in vacuo to afford methyl 5-amino-2-methoxy-4-(4-methoxybenzylamino)benzoate as a white solid (30.0 g, 75%).

Workup

  1. customto react for 2 h at room temperature under an atmosphere of H2 (g)
  2. filtrationThe solids were filtered from the resulting solution
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d0c309902daf467b8805af3322022059
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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