Ethyl 2-chloroacetoacetate → Ethyl 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxylate

HRID 1530048ノート

反応式

HRID 1530048 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[CH:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([CH3:17])[N:8]=2)[N:7]=1

参加物

4

反応物 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 216436-Amino-3-chloropyridazine

生成物 1

HCID 14091884Ethyl 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxylate収率 32.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 6-chloropyridazin-3-amine (5.3 g, 41 mmol), ethyl 2-chloro-3-oxobutanoate (6.7 g, 41 mmol) and ethanol (50 mL) was heated under reflux for 2 days. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution and ethyl acetate were added to the obtained residue, and the insoluble material was filtered off. The filtrate was extracted with ethyl acetate, and the collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the obtained residue, and the insoluble material was filtered off. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) and washed with ethyl acetate/diisopropyl ether to give the title compound (3.2 g, 32%) as a colorless solid.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution and ethyl acetate
  4. additionwere added to the obtained residue
  5. filtrationthe insoluble material was filtered off
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washthe collected organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. additionEthyl acetate and diisopropyl ether were added to the obtained residue
  12. filtrationthe insoluble material was filtered off
  13. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)
  14. washwashed with ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-1ae9ec5058ea4d898dffd96c38e2ce71
出典データセット
uspto-grants-2015_07
特許番号
US09090601B2

反応ノート

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