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

HRID 1992546Notes

Reaction equation

HRID 1992546 reaction equation
[CH3:1][CH2:2][O:3][CH2:4][C:5](Cl)=[O:6].[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][N:10]=1.CN1CCOCC1>ClCCl>[CH2:2]([O:3][CH2:4][C:5]([NH:16][NH:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][C:9]([Cl:8])=[N:10][CH:11]=1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 84189Ethoxyacetyl chlorideHCID 28001776-Chloropyridine-3-carbohydrazide

Product 1

HCID 589974826-Chloro-nicotinic Acid N'-(2-ethoxy-acetyl)-hydrazideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Ethoxy)-acetyl chloride [(1.72 g, 13.99 mmol), Tett. Lett., 35, (39), 7269; 1994)] 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 washed with citric acid, sodium hydrogen carbonate solution and brine and the solvent was evaporated under reduced pressure to yield some title product as a white solid, 880 mg. The combined aqueous washings were extracted with ethyl acetate (×2) and the combined organic solutions were dried over sodium sulfate and concentrated in vacuo to afford a further crop of title compound as a pale yellow solid, 1.6 g (total yield of 83%).

Workup

  1. washThe mixture was then washed with citric acid, sodium hydrogen carbonate solution and brine
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f71cac9d096145819156d30affc51361
Source dataset
uspto-grants-2010_01
Patent number
US07649003B2

Reaction notes

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