2-METHYL-4-NITRO-N,N-DIETHYLANILINE → N~1~,N~1~-Diethyl-2-methylbenzene-1,4-diamine

HRID 450095Notes

Reaction equation

HRID 450095 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[CH3:13])[CH3:2]>CO.[Pd]>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH3:13])[CH3:15]

Participants

4

Reactant 1

HCID 116298342-METHYL-4-NITRO-N,N-DIETHYLANILINE

Product 1

HCID 10313365N~1~,N~1~-Diethyl-2-methylbenzene-1,4-diamineYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of diethyl-(2-methyl-4-nitro-phenyl)-amine (340 mg, 1.634 mmol) in methanol (10 ml) was hydrogenated over 10% Pd—C (50 mg) at room temperature and atmospheric pressure until no more gas absorption occurred. The reaction mixture was filtered over celite and the filtrate concentrated to dryness to give N1,N1-Diethyl-2-methyl-benzene-1,4-diamine (243 mg, 46.5%) as oil.

Workup

  1. customatmospheric pressure until no more gas absorption
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-cf0c7725696a4b32b37936c84e424b14
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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