Phenylacetonitrile → HCID 20520018, compound

HRID 2198375Notes

Reaction equation

HRID 2198375 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH2:12]([C:19]#[N:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>O1CCOCC1>[C:19]([CH:12]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:20]

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 20520018HCID 20520018, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

There were gradually added to a cooled and stirred solution of 190 grams of 2,6-dichloro-3-nitropyridine and 117 grams of benzyl cyanide in 2 liters of dioxane under a nitrogen atmosphere 64 grams of sodium hydride (80% in white oil). The reaction mixture immediately turned a deep dark blue color, gradually a finely divided precipitate began to separate out, the temperature rose (with cooling with ice water) to 30° C. After 3 hours the mixture was treated with about 20 ml of ethyl alcohol, stirred for another 20 minutes, then filtered with suction. The deep blue sodium salt was dissolved in 1 liter of water, treated with dilute acetic acid until the color changed. The 2-(α-cyanobenzyl)-3-nitro-6-chloropyridine formed crystallized out in pure form. M.P. 165° C.; Yield 146 grams.

Workup

  1. additionThere were gradually added to
  2. temperaturea cooled
  3. customto separate out
  4. additionAfter 3 hours the mixture was treated with about 20 ml of ethyl alcohol
  5. filtrationfiltered with suction
  6. dissolutionThe deep blue sodium salt was dissolved in 1 liter of water
  7. additiontreated with dilute acetic acid until the color

Sources & evidence

ORD record
ord-68c6efe4365d45d58e46c6f04cc3eb4e
Source dataset
uspto-grants-1982_11
Patent number
USRE031071

Reaction notes

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