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Hydrochloric Acid → 1-Cyclopropanecarbonyl-2-(5,6-dichloro-3-pyridinecarbonyl)-hydrazine

HRID 368289
Notes
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Reaction equation

HRID 368289 reaction equation
[CH:1]1([C:4]([NH:6][NH2:7])=[O:5])[CH2:3][CH2:2]1.[Cl:8][C:9]1[C:10]([Cl:18])=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14](Cl)=[O:15].Cl>[OH-].[Na+].C(COC)OC>[CH:1]1([C:4]([NH:6][NH:7][C:14]([C:13]2[CH:12]=[N:11][C:10]([Cl:18])=[C:9]([Cl:8])[CH:17]=2)=[O:15])=[O:5])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 81396CyclopropanecarbohydrazideHCID 27821565,6-dichloropyridine-3-carbonyl Chloride

Product 1

HCID 232882651-Cyclopropanecarbonyl-2-(5,6-dichloro-3-pyridinecarbonyl)-hydrazineYield 35%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent
HCID 14798
Sodium Hydroxide
Solvent

Conditions

Temperature
0 °C

Procedure

A mixture of cyclopropanecarboxylic acid hydrazide (1.6 g, 16 mmol) in 5% aqueous sodium hydroxide (50 mL) was cooled to 0° C. with stirring and a solution of 5,6-dichloronicotinoyl chloride (3.1 g, 14.8 mmol) in dimethoxyethane (10 mL) added over 20 minutes. This was stirred at room temperature overnight, acidified to pH 3-4 with 1N hydrochloric acid and filtered. The resulting tan solid was dried to give the desired product (1.4 g, 35%).

Workup

  1. stirringThis was stirred at room temperature overnight
  2. filtrationfiltered
  3. customThe resulting tan solid was dried

Sources & evidence

ORD record
ord-fc1cecb051884870bd2b9f77aa13ef55
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133294

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes