(2-Methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amine → 4-methoxy-N1-(2-methoxy-ethyl)-N1-methyl-benzene-1,3-diamine

HRID 51839Notes

Reaction equation

HRID 51839 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([N+:15]([O-])=O)[CH:8]=1)[CH3:6]>CO.[Pd]>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])=[CH:8][C:9]=1[NH2:15]

Participants

4

Reactant 1

HCID 22736970(2-Methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amine

Product 1

HCID 227369974-methoxy-N1-(2-methoxy-ethyl)-N1-methyl-benzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2.50 g (10.4 mmol) (2-methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amine in 100 ml methanol was added a spatula end of 10% palladium on charcoal and the mixture was then stirred for 16 hours at room temperature under an atmosphere of hydrogen. The mixture was then filtered and the filtrate concentrated in vacuo to afford 1.90 g (87 (ho) 4-methoxy-N1-(2-methoxy-ethyl)-N1-methyl-benzene-1,3-diamine as an off-white crystalline solid. ES-MS m/e (%): 211 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d8b1b0948c6d4cfbb28598808defdb52
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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