Methylamine → N-methyl-1-(4-nitrophenyl)methanamine

HRID 322628

Reaction equation

HRID 322628 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][NH2:13]>C(#N)C.[Cl-].[Na+].O>[CH3:12][NH:13][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 409440N-methyl-1-(4-nitrophenyl)methanamineYield 97.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of p-nitrobenzylbromide (5.40 g, 25 mmol) in acetonitrile (60 ml) is added dropwise to a stirred solution of aqueous methylamine (65 mL, 40 wt. %, 0.75 mol) in acetonitrile (50 mL) at 0°. After stirring an additional 15 minutes, the solution is poured into brine and extracted 2× with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 4-(methylaminomethyl)nitrobenzene (4.04 g).

Workup

  1. extractionextracted 2× with dichloromethane
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfe81d4002ef4017b05c7d4ca92b6a8f
Source dataset
uspto-grants-2001_04
Patent number
US06211365B1

Linked notes

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