4-Nitrobenzyl chloride → HCID 4719099, compound

HRID 552126Notes

Reaction equation

HRID 552126 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:19]([NH2:21])[CH3:20]>C(#N)C>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:21][CH2:19][CH3:20])=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 11198Ethylamine hydrochlorideHCID 11430Potassium Carbonate

Product 1

HCID 4719099HCID 4719099, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 0.34 g (2.0 mmol, 1.0 eq.) of 1-(chloromethyl)-4-nitrobenzene and 1.38 g (10 mmol, 5.0 eq.) of potassium carbonate in 20 mL of acetonitrile was added 0.33 g (4.0 mmol, 2.0 eq.) ethylamine hydrochloride. The reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature, filtered and the solvent removed in vacuo to provide 0.18 g (1.0 mmol, 50%) of N-(4-nitrobenzyl)ethanamine (I-29).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a94377d76c3c42bd94fb13a4713b7844
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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