Sodium Cyanide → 9-Acridinecarbonitrile, 2-chloro-

HRID 1576240Notes

Reaction equation

HRID 1576240 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5](Cl)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C-:17]#[N:18].[Na+]>CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:17]#[N:18])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 122961192,9-DICHLOROACRIDINE

Product 1

HCID 71036109-Acridinecarbonitrile, 2-chloro-Yield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 gm of 2,9-dichloroacridine [obtained by the process of Bogucka, Roczniki, Chem. Vol. 40 (1966) p 677] 230 mg of sodium cyanide and 20 cc of methanol was heated for 4 hours at 140°C in a sealed tube and after cooling, the mixture was filtered. The precipitate was washed with acetone and dried. The product was purified by sublimation in vacuo at 0.1 mm Hg to obtain 530 mg of 2-chloro-9-cyano-acridine melting at 208°C.

Workup

  1. customobtained by the process of Bogucka, Roczniki, Chem
  2. temperatureafter cooling
  3. filtrationthe mixture was filtered
  4. washThe precipitate was washed with acetone
  5. customdried
  6. customThe product was purified by sublimation in vacuo at 0.1 mm Hg

Sources & evidence

ORD record
ord-c55b58d057e445e18b4f5f5bc928a8d3
Source dataset
uspto-grants-1976_09
Patent number
US03979515

Reaction notes

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