2,5-Dichloronitrobenzene → HCID 18509329, compound

HRID 1356626Notes

Reaction equation

HRID 1356626 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:15])[CH2:14][CH2:13]1>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:15][CH:12]2[CH2:14][CH2:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

3

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 69828Cyclopropylamine

Product 1

HCID 18509329HCID 18509329, compoundYield 59%

Procedure

A mixture of 2,5-dichloronitrobenzene (2.00 g (10.4 mmol)) and cyclopropylamine (2.0 ml) was heated under reflux for 60 hours, and the excess cyclopropylamine was removed by concentration under reduced pressure. The residue was dissolved in ethyl acetate and the resulting solution was washed with aqueous 1% sodium hydroxide, saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:10) as eluent to give 1.30 g (59%) of 4-chloro-N-cyclopropyl-2-nitroaniline as orange crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 60 hours
  3. customthe excess cyclopropylamine was removed by concentration under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe resulting solution was washed with aqueous 1% sodium hydroxide, saturated sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f96f33e0454a490d864438bf678888bd
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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