Potassium Cyanide → 2-Amino-2-cyano-8-chloro-1,2,3,4-tetrahydronaphthalene

HRID 375583Notes

Reaction equation

HRID 375583 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[C-:13]#[N:14].[K+].[Cl-].[NH4+:17]>CO.O>[NH2:17][C:9]1([C:13]#[N:14])[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 46232698-Chloro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 118203212-Amino-2-cyano-8-chloro-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a vigorously stirred solution, maintained under nitrogen, containing 277 mmol of 8-chloro-3,4-dihydro-2(1H)-naphthalenone in 350 ml of methanol and 170 ml of water are successively added 282 mmol of potassium cyanide and 290 mmol of ammonium chloride. After stirring for 48 hours at 20° C., the mixture is concentrated. The residue is taken up in ethyl acetate. This organic phase is washed with water and extracted with 1N hydrochloric acid. The acidic phases are basified with 35% sodium hydroxide and extracted with ethyl acetate. The expected product is obtained, in solid form, after drying and evaporating the organic phases.

Workup

  1. temperatureTo a vigorously stirred solution, maintained under nitrogen
  2. concentrationthe mixture is concentrated
  3. washThis organic phase is washed with water
  4. extractionextracted with 1N hydrochloric acid
  5. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-cd01ce221b9f41a49778619f4d3f5ee8
Source dataset
uspto-grants-1996_01
Patent number
US05486532

Reaction notes

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