4-Methoxybenzylamine → 5-bromo-N-(4-methoxybenzyl)-2-nitroaniline

HRID 1051451Notes

Reaction equation

HRID 1051451 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 653416735-bromo-N-(4-methoxybenzyl)-2-nitroanilineYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (500 mg, 2.27 mmol) in DMF (6 mL) was added (4-methoxyphenyl)methanamine (342 mg, 2.5 mmol) and TEA (345 mg, 3.4 mmol). The reaction mixture was then stirred at 120° C. for 30 min under microwave heating. After cooling, the mixture was diluted with water (40 mL) and the resulting precipitate collected by filtration, washed with water and dried in vacuo to give the desired product (750 mg, crude, 97% yield) which was used in next step without further purification. LCMS (m/z): 338.1 [M+H]+

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9fcfd0cf818146d08227ce4cf5012721
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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