Sodium Cyanide → 7-cyano-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

HRID 542818노트

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HRID 542818 반응식
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[C-:20]#[N:21].[Na+]>C(#N)C>[C:20]([C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1)#[N:21]

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 134744537-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

생성물 1

HCID 134744277-cyano-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone (5.25 g), sodium cyanide (1.0 g), crown ether (18-crown-6, 5.4 g) and acetonitrile (200 ml) was stirred and boiled under reflux for 79 hours, left at ambient temperature for 70 hours, and boiled under reflux for 24 hours. The mixture was cooled and filtered. The residue was boiled with industrial methylated spirit (200 ml) and the mixture filtered while hot. The residue was further extracted twice with boiling 50% aqueous industrial methylated spirit (400 ml, then 200 ml). Each hot extract precipitated a solid when cooled. The three solids were combined and recrystallised from 50% aqueous industrial methylated spirit to give a crude product. This product was purified by high pressure liquid chromatography on silica, using dichloromethane:methanol 9:1 as the eluent. The eluent was evaporated to give a residue which was recrystallised from 30% aqueous industrial methylated spirit to give the novel compound 7-cyano-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. 301°-303°.

후처리

  1. temperatureunder reflux for 79 hours
  2. temperatureunder reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. filtrationthe mixture filtered while hot
  6. extractionThe residue was further extracted twice
  7. extractionEach hot extract
  8. customprecipitated a solid when
  9. temperaturecooled
  10. customrecrystallised from 50% aqueous industrial methylated spirit
  11. customto give a crude product
  12. customThis product was purified by high pressure liquid chromatography on silica
  13. customThe eluent was evaporated
  14. customto give a residue which
  15. customwas recrystallised from 30% aqueous industrial methylated spirit

출처 및 근거

ORD 기록
ord-b74d5d2379974cc28e09f0aa01e93b51
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659718

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