Hydrochloric Acid → HCID 1079140, compound

HRID 1955579Notes

Reaction equation

HRID 1955579 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:11][C:12]1[C:21](N)=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.O>CO>[CH2:1]([C:8]1[NH:9][C:21]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[CH:18]3)=[CH:13][C:12]=2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8794PhenylacetonitrileHCID 698722,3-Diaminonaphthalene

Product 1

HCID 1079140HCID 1079140, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 1M solution of benzyl cyanide in anhydrous methanol is treated with hydrogen chloride gas at 0° C. for about thirty minutes. The mixture is stirred for two hours at 0° C. and then a 1M solution of 2,3-diaminonaphthalene is added and the resulting solution is stirred at 0° C. The progress of the reaction is monitored by thin layer chromatography. The reaction mixture is then poured into water. The unreacted nitrile is extracted with ethyl acetate. The aqueous layer is neutralized with 1N sodium hydroxide. The organic fraction is extracted with ethyl acetate and condensed. The desired title product is recrystallized from methanol/water.

Workup

  1. stirringthe resulting solution is stirred at 0° C
  2. extractionThe unreacted nitrile is extracted with ethyl acetate
  3. extractionThe organic fraction is extracted with ethyl acetate and condensed
  4. customThe desired title product is recrystallized from methanol/water

Sources & evidence

ORD record
ord-221f2bd05b14490fad32b75bb3f177e2
Source dataset
uspto-grants-1998_07
Patent number
US05776931

Reaction notes

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