Water → (2-Nitrophenyl)(2-phenylethyl)amine

HRID 1189262Notes

Reaction equation

HRID 1189262 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1([CH2:17][CH2:18][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CCO>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:19][CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 1001Phenethylamine2×HCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2920933(2-Nitrophenyl)(2-phenylethyl)amineYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-fluoro-2-nitrobenzene (4.4 g, 31.2 mmol) in EtOH (32 mL) was added at 0° C., 2-phenylethanamine (4.11 mL, 32.8 mmol). Mixture went from light yellow to bright orange instantly and it was stirring overnight at RT. Another equivalent of 2-phenylethanamine was added (4.11 mL, 32.8 mmol) and the mixture was heated to 50° C. overnight. Water was added (20 ml) and the resulting orange solid was isolated by filtration to afford 6.99 g of 2-nitro-N-phenethylbenzenamine (Yield: 92%) as an orange crystalline solid.

Workup

  1. temperaturethe mixture was heated to 50° C. overnight
  2. customthe resulting orange solid was isolated by filtration

Sources & evidence

ORD record
ord-a4cc02945d5042f6832d02bb3cd8c6ee
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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