Hydrochloric Acid → HCID 18315411, compound

HRID 276004Notes

Reaction equation

HRID 276004 reaction equation
[ClH:1].ClC1C=[CH:24][CH:23]=[CH:22][C:4]=1[CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([NH2:15])=O)=O>O1CCOCC1>[Cl:1][C:5]1[CH:4]=[CH:22][CH:23]=[CH:24][C:6]=1[CH2:7][NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]#[N:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57182773HCID 57182773, compound

Product 1

HCID 18315411HCID 18315411, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

One milliliter of 35% hydrochloric acid was added to a solution of 850 mg of 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzamide in 10 ml of 1,4-dioxane, and the mixture was heat-refluxed for 4 days. After the solvent was distilled off from the reaction solution under reduced pressure, the residue was separated by being poured in a mixture solution of water and chloroform. The organic layer was washed with water, and was dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified through column chromatography [50 ml, chloroform] to give 230 mg of 3-[N-(2-chlorobenzyl)amino]-4-nitrobenznitrile.

Workup

  1. temperaturethe mixture was heat-refluxed for 4 days
  2. distillationAfter the solvent was distilled off from the reaction solution under reduced pressure
  3. customthe residue was separated
  4. additionby being poured in a mixture solution of water and chloroform
  5. washThe organic layer was washed with water
  6. dry with materialwas dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified through column chromatography [50 ml, chloroform]

Sources & evidence

ORD record
ord-2fb70916bb68425db8e09d2eac470b9c
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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