1,2-Dichloro-3-(4-nitrobenzyl)benzene → 4-(2,3-Dichlorobenzyl)phenylamine

HRID 491515Notes

Reaction equation

HRID 491515 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:3]=1[Cl:18]>C(O)(=O)C.[Zn]>[Cl:18][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 30173791,2-Dichloro-3-(4-nitrobenzyl)benzene

Product 1

HCID 230839364-(2,3-Dichlorobenzyl)phenylamineYield 81%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml), zinc powder (70 g, 1.1 mol) was added by portions at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite and washed with ethanol. The filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml), 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with n-hexane and vacuum dried to give the object product (18.1 g, yield 81%) as a pale-brown solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationthe precipitated solid was collected by filtration on the way
  5. washThe filtrated solid was washed with diethyl ether
  6. dissolutiondissolved in ethyl acetate (500 ml)
  7. additionwater (500 ml), 4N aqueous sodium hydroxide solution was added
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was further extracted with ethyl acetate
  10. washThe organic layers were combined washed with water and saturated brine
  11. dry with materialdried over sodium sulfate
  12. filtrationAfter filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. filtrationthe precipitated solid was collected by filtration on the way
  15. washThe filtrated solid was washed with n-hexane and vacuum
  16. customdried

Sources & evidence

ORD record
ord-20778bb43f3049149076ae8b5e31a035
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

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