Methane → 2-(Methoxymethyl)aniline

HRID 339005Notes

Reaction equation

HRID 339005 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O.[H][H].C>CO.O=[Pt]=O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10]

Participants

6

Reactant 3

HCID 297MethaneHCID 126166891-(Methoxymethyl)-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 123343062-(Methoxymethyl)anilineYield 97%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(methoxymethyl)-2-nitrobenzene (4.30 g, 25.7 mmol) and PtO2 (0.29 g, 1.29 mmol) in MeOH (30 mL) was charged with 1 atmosphere hydrogen and stirred at ambient temperature for 1 hour. Charcoal (5 g) was added and the reaction mixture was stirred for 10 minutes. The solid was removed by filtration and washed with methanol. The filtrate was concentrated under reduced pressure to give 2-(methoxymethyl)aniline (3.42 g, 96.9%) as a solid.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customThe solid was removed by filtration
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7367e47b3244552ae1321ad6a778546
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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