Ammonia → HCID 68142773, compound

HRID 918231

Reaction equation

HRID 918231 reaction equation
[Na].N.[C:3](#[N:5])[CH3:4].[C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)#[N:7]>C(OCC)C>[NH2:7][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[CH:4][C:3]#[N:5]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 6342Acetonitrile2×HCID 119442-NaphthalenecarbonitrileHCID 5360545Sodium

Product 1

HCID 68142773HCID 68142773, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.0 grams (0.087 mole) of sodium in 125 milliliters of liquid ammonia was added a solution of 3.67 grams (0.089 mole) of acetonitrile in 10 milliliters of diethyl ether over a period of about five minutes. The reaction mixture was then cooled in a dry ice-acetone bath and a solution of 10.0 grams (0.065 mole) of 2-cyanonaphthalene in a minimum of dry diethyl ether was rapidly added within about five minutes after completion of the acetonitrile addition. The reaction mixture was stirred for about one and one-half hours and the ammonia was then allowed to evaporate. Water was cautiously added to the reaction mixture under nitrogen and the resulting mixture was extracted with diethyl ether. The ether was separated and the residue recrystallized from a mixture of chloroform and hexane. There was obtained 2.8 grams (22% of theoretical) of β-amino-β-(2-naphthyl)acrylonitrile, melting point 85°-90°C. Analysis: -- Calculated for C13H10N2 (percent): C, 80.39; H, 5.19; N, 14.42. Found (percent): C, 80.08; H, 4.99; N, 14.06.

Workup

  1. temperatureThe reaction mixture was then cooled in a dry ice-acetone bath
  2. customto evaporate
  3. additionWater was cautiously added to the reaction mixture under nitrogen
  4. extractionthe resulting mixture was extracted with diethyl ether
  5. customThe ether was separated
  6. customthe residue recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-afe1ff5f551f458494fbceedb140abd7
Source dataset
uspto-grants-1976_07
Patent number
US03970622

Linked notes

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