4-Methylmorpholine → 6-Chloro-nicotinic Acid N'-[2-(2-methoxy-ethoxy)-acetyl]-hydrazide

HRID 254251

反応式

HRID 254251 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](Cl)=[O:8].[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([NH:17][NH2:18])=[O:16])=[CH:13][N:12]=1.CN1CCOCC1.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([NH:18][NH:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([Cl:10])=[N:12][CH:13]=1)=[O:8]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 28001776-Chloropyridine-3-carbohydrazideHCID 70103382-(2-Methoxyethoxy)acetyl chloride

生成物 1

HCID 589974306-Chloro-nicotinic Acid N'-[2-(2-methoxy-ethoxy)-acetyl]-hydrazide収率 51%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

(2-Methoxy-ethoxy)-acetyl chloride (2.13 g, 13.99 mmol) was added to an ice-cold solution of 6-chloronicotinic acid hydrazide (2 g, 11.66 mmol) and N-methylmorpholine (1.92 mL, 17.49 mmol) in dichloromethane (60 mL) and the mixture was stirred at room temperature for 18 hours. The mixture was then treated with sodium hydrogen carbonate solution and concentrated in vacuo. The aqueous residue was extracted with dichloromethane (×2) and the combined organic solutions were washed with brine and dried over sodium sulfate and concentrated in vacuo to give a pale yellow residue. The residue was then stirred in diethyl ether for 2 hours, filtered and dried to afford the title compound as a pale yellow solid in 51% yield, 1.7 g.

後処理

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous residue was extracted with dichloromethane (×2)
  3. washthe combined organic solutions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a pale yellow residue
  7. filtrationfiltered
  8. customdried

出典と根拠

ORDレコード
ord-3d8be728137444bebfe65289ba627e72
出典データセット
uspto-grants-2011_01
特許番号
US07875615B2

関連ノート

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