3-methoxy-N-methyl-2-nitroaniline → 3-methoxy-N1-methylbenzene-1,2-diamine

HRID 408094Notes

Reaction equation

HRID 408094 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-])=O)=[C:5]([NH:9][CH3:10])[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][CH3:10])[C:4]=1[NH2:11]

Participants

4

Reactant 1

HCID 580715913-methoxy-N-methyl-2-nitroaniline

Product 1

HCID 106069363-methoxy-N1-methylbenzene-1,2-diamineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7.4 g (3-methoxy-2-nitrophenyl)-methylamine are suspended in 150 ml of ethyl acetate and hydrogenated with 1 g Pd/C 10% at a pressure of 50 psi and at ambient temperature. After 4.5 hours the catalyst is suction filtered and the filtrate is evaporated to dryness. 5.9 g of the product are obtained as an oil.

Workup

  1. filtrationsuction filtered
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-55e2faf7537d4f5d9580a088716d65b6
Source dataset
uspto-grants-2014_06
Patent number
US08759326B2

Reaction notes

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