2-Methoxy-4-methoxymethyl-1-nitro-benzene → 2-Methoxy-4-(methoxymethyl)aniline

HRID 1821791Notes

Reaction equation

HRID 1821791 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[CH:5][C:4]=1[N+:12]([O-])=O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[CH:5][C:4]=1[NH2:12]

Participants

4

Reactant 1

HCID 220465272-Methoxy-4-methoxymethyl-1-nitro-benzene

Product 1

HCID 220465282-Methoxy-4-(methoxymethyl)anilineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL Parr apparatus, 2.1 g (10.6 mmol) of 2-methoxy-4-methoxymethyl-1-nitro-benzene, in 40 mL of ethanol was hydrogenated at 2 atm over 300 mg of 10% Pd on carbon for 2.5 h. The catalyst was removed by filtration through a glass fiber filter and the filtrate was concentrated to give 1.61 g (91%) of product as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 6.80 (s, 1H), 6.74 (d, J=7.8 Hz, 1H), 6.67 (d, J=7.8 Hz), 4.35 (s, 2H), 3.86 (s, 3H), 3.78 (br d, 2H), 3.35 (s, 3H). MS ESI-pos, M+1=168.1.

Workup

  1. customThe catalyst was removed by filtration through a glass fiber
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c63b2d119aef4a91961f24ec7ab7873f
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

Loading…