Acetic Acid → 2-Chloro-5-fluoropyridine-3-carboxamide

HRID 536475노트

반응식

HRID 536475 반응식
[Cl:1][C:2]1[N:10]=[C:9](Cl)[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(O)(=O)C>CO.[Zn]>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 27740222,6-Dichloro-5-fluoronicotinamide

생성물 1

HCID 126297962-Chloro-5-fluoropyridine-3-carboxamide

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

44 g (210.58 mmol) of 2,6-dichloro-5-fluoronicotinamide was added at RT to a suspension of 21.9 g (335.35 mmol) of zinc in methanol (207 ml). Then acetic acid (18.5 ml) was added and it was heated under reflux for 24 h, with stirring. Then the flask contents were decanted from the zinc and ethyl acetate (414 ml) and saturated aqueous sodium hydrogen carbonate solution (414 ml) were added and stirred vigorously. Then it was filtered with suction on diatomaceous earth and washed again three times with ethyl acetate (517 ml each time). The organic phase was separated and the aqueous phase was washed with ethyl acetate (258 ml). The combined organic phases were washed once with saturated aqueous sodium hydrogen carbonate solution (414 ml), dried and concentrated by vacuum evaporation. Dichloromethane (388 ml) was added to the crystals thus obtained, and left to precipitate for 20 min. It was filtered with suction again and washed with diethyl ether and suction-dried.

후처리

  1. temperatureit was heated
  2. temperatureunder reflux for 24 h
  3. customThen the flask contents were decanted from the zinc and ethyl acetate (414 ml) and saturated aqueous sodium hydrogen carbonate solution (414 ml)
  4. additionwere added
  5. stirringstirred vigorously
  6. filtrationThen it was filtered with suction on diatomaceous earth
  7. washwashed again three times with ethyl acetate (517 ml each time)
  8. customThe organic phase was separated
  9. washthe aqueous phase was washed with ethyl acetate (258 ml)
  10. washThe combined organic phases were washed once with saturated aqueous sodium hydrogen carbonate solution (414 ml)
  11. customdried
  12. concentrationconcentrated by vacuum evaporation
  13. additionDichloromethane (388 ml) was added to the crystals
  14. customthus obtained
  15. waitleft
  16. customto precipitate for 20 min
  17. filtrationIt was filtered with suction again
  18. washwashed with diethyl ether
  19. customsuction-dried

출처 및 근거

ORD 기록
ord-dd4bd298932b4155a96861035740d51e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859569B2

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