Water → 5-bromo-2-nitro-N-propylbenzenamine

HRID 1966425Notes

Reaction equation

HRID 1966425 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.C(N(C(C)C)CC)(C)C.[CH2:21]([NH2:24])[CH2:22][CH3:23].O>CN1C(=O)CCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:24][CH2:21][CH2:22][CH3:23])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 584256215-bromo-2-nitro-N-propylbenzenamineYield 95.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (0.5 g, 2.29 mmol) and diisopropyl ethyl amine (1.38 mL, 3.44 mmol) in NMP (5 mL) was added propylamine (0.22 mL, 2.7 mmol). The solution was stirred for 14 h to which was slowly added H2O (5 mL). The resulting yellow precipitate was filtered, washed with 2 mL of water, subjected to high vacuum for drying for 14 h to furnish 5-bromo-2-nitro-N-propylbenzenamine (520 mg, 2.18 mmol), 92% yield, which was used without further purification.

Workup

  1. filtrationThe resulting yellow precipitate was filtered
  2. washwashed with 2 mL of water
  3. customfor drying for 14 h

Sources & evidence

ORD record
ord-078c2981e13149298207f785a6ba8513
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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