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

HRID 1046069ノート

反応式

HRID 1046069 の反応式
[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

参加物

4

反応物 2

HCID 584852976-chloro-N-methoxy-N-methylpyridazine-3-carboxamideHCID 178418689HCID 178418689、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-feeb478af4ea436d82b1a8cfcfe7b5ea
出典データセット
uspto-grants-2013_10
特許番号
US08569292B2

反応ノート

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