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

HRID 1067598ノート

反応式

HRID 1067598 の反応式
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl[CH:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([CH3:17])[N:1]=2)[N:4]=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 12.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

12.9 g of 3-amino-6-chloropyridazine was suspended in 250 ml of ethanol; 18.1 g of ethyl 2-chloro-3-oxobutanoate was added, followed by thermal refluxing for 6 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was ajusted to pH 7 by the addition of aqueous sodium bicarbonate; ethyl ether was added; the precipitated was collected by filtration and extracted with ethyl ether; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; ethanol-1 N aqueous solution of sodium hydroxide (1:1) was added; the crystal precipitated was collected by filtration; the filtrate was concentrated again. The residue was crystallized by the addition of ethyl acetate and collected by filtration to yield 3.09 g of the title compound.

後処理

  1. customrefluxing for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionthe residue was ajusted to pH 7 by the addition of aqueous sodium bicarbonate
  5. additionethyl ether was added
  6. filtrationthe precipitated was collected by filtration
  7. extractionextracted with ethyl ether
  8. washthe extract was washed with saturated saline
  9. dry with materialdried with magnesium sulfate
  10. concentrationThe dry product was concentrated under reduced pressure
  11. additionethanol-1 N aqueous solution of sodium hydroxide (1:1) was added
  12. customthe crystal precipitated
  13. filtrationwas collected by filtration
  14. concentrationthe filtrate was concentrated again
  15. customThe residue was crystallized by the addition of ethyl acetate
  16. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-00889c66e5854662b5802d157ae14b44
出典データセット
uspto-grants-2001_06
特許番号
US06248740B1

反応ノート

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