Acetonitrile → HCID 70357837, compound

HRID 330516Notes

Reaction equation

HRID 330516 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](CCl)=[CH:7]2.[C-]#N.[Na+].[CH3:17][C:18]#[N:19]>O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:17][C:18]#[N:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8929Sodium CyanideHCID 146963871-Chloro-6-(chloromethyl)naphthalene

Product 1

HCID 70357837HCID 70357837, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-chloromethylnaphthalene (1.37 g crude product, 5.12 mmol), NaCN (0.275 g, 5.61 mmol), CH3CN (10 mL), and H2O (1 mL) was heated under reflux for 5.5 hours, cooled, and stirred at room temperature overnight. The mixture was partitioned between ether and H2O. The aqueous phase was extracted with ether, and the combined ether layers were washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (eluant EtOAc/hexane (10:90)) gave a pale yellow solid (600 mg, 58%), m.p. 95°-98° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5.5 hours
  3. temperaturecooled
  4. customThe mixture was partitioned between ether and H2O
  5. extractionThe aqueous phase was extracted with ether
  6. washthe combined ether layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (eluant EtOAc/hexane (10:90))

Sources & evidence

ORD record
ord-11511cca37b04c73aa9309da00af4934
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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