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

HRID 254251

반응식

HRID 254251 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d8be728137444bebfe65289ba627e72
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875615B2

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