Methyl 4-(methylamino)-3-nitrobenzoate → Methyl 3-amino-4-(methylamino)benzoate

HRID 1393686Notes

Reaction equation

HRID 1393686 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O.[H][H]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[NH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[NH:2][CH3:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 7650848Methyl 4-(methylamino)-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 15586064Methyl 3-amino-4-(methylamino)benzoateYield 62%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The methyl 4-methylamino-3-nitrobenzoate (6.3 g) obtained above was suspended in 1,4-dioxane (125 ml). 20% Palladium hydroxide (6.3 g) was added thereto, and the mixture was stirred for 91 hours at room temperature in a hydrogen atmosphere. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:4→2:3) to give methyl 3-amino-4-methylaminobenzoate (3.3 g, Y.:62%).

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:4→2:3)

Sources & evidence

ORD record
ord-83aa1b2cba0b486c971159a095b475fd
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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