Water → Ethyl[(2-nitrophenyl)methyl]amine

HRID 1006016Notes

Reaction equation

HRID 1006016 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].[CH2:12]([NH2:14])[CH3:13].O.[OH-].[Na+]>O1CCCC1>[CH2:12]([NH:14][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 14798Sodium HydroxideHCID 77569alpha-Bromo-2-nitrotoluene

Product 1

HCID 14485081Ethyl[(2-nitrophenyl)methyl]amineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitrobenzylbromide (0.23 mol) in tetrahydrofuran (500 ml) was added to a stirred mixture (4.35M) of 70% aqueous ethylamine (350 ml) and water (350 ml) over a 20 minutes. The reaction stood at ambient temperature for 1 hour, was reduced to low volume, treated with ice/water to 800 ml and basified with an aqueous solution of sodium hydroxide (ION, 23 ml). It was extracted with ether (2×) and the combined extracts dried (MgSO4) and evaporated to give N-ethyl-2-nitrobenzylamine as a yellow oil (44 g, 100%).

Workup

  1. extractionIt was extracted with ether (2×)
  2. dry with materialthe combined extracts dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-1c68dc2e8ca34cae89c61d9ccefed3c9
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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