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

HRID 375582Notes

Reaction equation

HRID 375582 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]>C(O)C.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 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a vigorously stirred solution, maintained under nitrogen, containing 43 mmol of 8-chloro-3,4-dihydro-2(1H)-naphthalenone in 60 ml of ethanol and 30 ml of water are successively added 44 mmol of potassium cyanide and 44 mmol of ammonium chloride. After stirring for 20 hours at 20° C., the mixture is concentrated under vacuum and the residue is taken up in 80 ml of ethyl acetate. This organic phase is washed with water and is then extracted with 1N hydrochloric acid. The aqueous phase is basified with 35% sodium hydroxide and extracted with ethyl acetate. The expected product is obtained after drying and evaporation of the organic phase as a solid.

Workup

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

Sources & evidence

ORD record
ord-031578e29954467f8906bc97d4ca025f
Source dataset
uspto-grants-1996_01
Patent number
US05486532

Reaction notes

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