Methanol → HCID 18315421, compound

HRID 1276865Notes

Reaction equation

HRID 1276865 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)[C:9]#[N:10].CO.[H][H]>[Pd].O1CCOCC1>[NH2:14][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[NH:5][CH2:4][C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 18315411HCID 18315411, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18315421HCID 18315421, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Fifty milligrams of 10% palladium on carbon were added to a mixed solution of 261 mg of 3-[N-(2-chlorobenzyl)amino]-4-nitrobenznitrile, 15 ml of methanol and 3 ml of 1,4-dioxane to conduct the catalytic reduction in a hydrogen atmosphere at 3 atm. After the completion of the reaction, the reaction solution was filtered through celite, and the filtrate was distilled off under reduced pressure. The resulting solid material was washed with ether, and was collected through filtration to give 196 mg of 4-amino-3-[N-(2-chlorobenzyl)amino]benznitrile.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction solution was filtered through celite
  3. distillationthe filtrate was distilled off under reduced pressure
  4. washThe resulting solid material was washed with ether
  5. filtrationwas collected through filtration

Sources & evidence

ORD record
ord-ccc0374814974269919cb16c7dea6a60
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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