Chloroacetyl chloride → 6-Chloro-nicotinic Acid N'-(2-chloro-acetyl)-hydrazide

HRID 1591706Notes

Reaction equation

HRID 1591706 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([NH:13][NH2:14])=[O:12])=[CH:9][N:8]=1.CN1CCOCC1>ClCCl>[Cl:1][CH2:2][C:3]([NH:14][NH:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:7]([Cl:6])=[N:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 28001776-Chloropyridine-3-carbohydrazide

Product 1

HCID 589974626-Chloro-nicotinic Acid N'-(2-chloro-acetyl)-hydrazideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (2.8 mL, 34.9 mmol) was added dropwise to an ice-cooled solution of 6-chloronicotinic acid hydrazide (5 g, 29.1 mmol) and 4-methylmorpholine (4.8 mL, 43.7 mmol) in dichloromethane (100 mL) and the reaction was stirred at room temperature for 3 hours. The resulting precipitate was then filtered off, slurried with dichloromethane, re-filtered, washed with dichloromethane (×3) and dried to afford the title compound as a beige solid in 57% yield, 4.1 g

Workup

  1. filtrationThe resulting precipitate was then filtered off
  2. filtrationre-filtered
  3. washwashed with dichloromethane (×3)
  4. customdried

Sources & evidence

ORD record
ord-4a16410dac9b457bb7d8b8655170f500
Source dataset
uspto-grants-2007_11
Patent number
US07291640B2

Reaction notes

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