Hydrochloric Acid → HCID 178489422, compound

HRID 1441111Notes

Reaction equation

HRID 1441111 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Na+].Cl>[Cl-].[Zn+2].[Cl-].CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]1[NH:13][N:12]=[N:11][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 810862-Methoxybenzonitrile

Product 1

HCID 178489422HCID 178489422, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared by the procedure of Example 1 using 2-methoxybenzonitrile, zinc chloride, sodium azide and N,N-dimethylformamide. The reaction is heated at reflux temperature for 5 hours, acidified with 10% hydrochloric acid, extracted with ethyl acetate, dried and concentrated in vacuo. The residue is chromatographed (silica gel: 50% ethyl acetate/methylene chloride) to give 2.57 g (yield=36% of theory).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux temperature for 5 hours
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed (silica gel: 50% ethyl acetate/methylene chloride)
  7. customto give 2.57 g (yield=36% of theory)

Sources & evidence

ORD record
ord-a6cee3aa8af54b8294a0140e41fa0f2b
Source dataset
uspto-grants-1996_03
Patent number
US05502191

Reaction notes

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