6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide → 1-(6-Chloropyridazin-3-yl)ethan-1-one

HRID 1046069노트

반응식

HRID 1046069 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](N(OC)C)=[O:9])=[CH:4][CH:3]=1.[CH3:14][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](=[O:9])[CH3:14])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 584852976-chloro-N-methoxy-N-methylpyridazine-3-carboxamideHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 468356481-(6-Chloropyridazin-3-yl)ethan-1-one수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide (13.5 g, 0.0659 mol) in THF (600 mL) was added CH3MgBr (43.2 ml, 0.13 mol) at −78° C. under N2. The reaction mixture was stirred at −78° C. for 2 h, quenched by addition of aq NH4Cl and filtered. The filtrate was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed under vacuum, and the residue was purified by column chromatography to afford 1-(6-chloropyridazin-3-yl)ethanone. (9.3 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 8.03 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 2.81 (s, 3H).

후처리

  1. customquenched by addition of aq NH4Cl
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum
  8. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-feeb478af4ea436d82b1a8cfcfe7b5ea
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569292B2

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