Methanol → N-(2-methyl-3-nitrobenzyl)-1-ethanamine

HRID 1822866Notes

Reaction equation

HRID 1822866 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH2:13]([NH2:15])[CH3:14].CO.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:15][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 6341EthylamineHCID 11430Potassium CarbonateHCID 108947alpha-Chloro-2-methyl-3-nitrotoluene

Product 1

HCID 22170308N-(2-methyl-3-nitrobenzyl)-1-ethanamineYield 87.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-3-nitrobenzylchloride (0.50 g, 2.7 mmol) and ethylamine (2.76 g, 61.2 mmol) in THF (10 ml)/MeOH (5 ml) was stirred at ambiend temperature for 48 h. The solvent was reduced and the recidue was dissolved in EtOAc/aq. K2CO3 solution. The aqueous phase was extracted with EtOAc (×2). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to give the title compound 0.46 g (86%) as a yellow oil.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a2bf77eea6e747bdb65d29a0e626c0aa
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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