4-Methylmorpholine → 6-Chloro-nicotinic Acid N'-[2-(2-methoxy-ethoxy)-acetyl]-hydrazide
Reaction equation
[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]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(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.
Workup
- concentrationconcentrated in vacuo
- extractionThe aqueous residue was extracted with dichloromethane (×2)
- washthe combined organic solutions were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customto give a pale yellow residue
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-449789447d1d438883514f1bb563bd93
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649003B2
Reaction notes
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