Methanol → HCID 136342830, compound

HRID 2232173Notes

Reaction equation

HRID 2232173 reaction equation
[Cl:1][C:2]1[N+:11]([O-:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1C(OC)=O.[NH2:14][NH2:15].[CH3:16][OH:17]>C(O)(C)C>[Cl:13][C:10]1[CH:9]=[C:8]([C:16]([NH:14][NH2:15])=[O:17])[CH:3]=[C:2]([Cl:1])[N+:11]=1[O-:12]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 9321HydrazineHCID 14006448HCID 14006448, compound

Product 1

HCID 136342830HCID 136342830, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a cold stirred mixture of 8.75 g (0.039 mole) of methyl 2,6-dichloronicotinate N-oxide in 50 ml of methanol was added dropwise 2.0 g (0.063 mole) of hydrazine in 14 ml of methanol. After complete addition the mixture was stirred for one hour then placed in a freezer for approximately 18 hours. The solvent was then removed by distillation under reduced pressure to leave a solid. The solid was stirred in isopropanol then filtered. The filter cake was added to 75 ml of refluxing ethanol and the resulting mixture filtered hot to yield 4.3 g of 2,6-dichloro-4-pyridinecarboxylic acid hydrazide 1-oxide as a solid.

Workup

  1. additionAfter complete addition the mixture
  2. stirringwas stirred for one hour
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customto leave a solid
  5. filtrationthen filtered
  6. additionThe filter cake was added to 75 ml of refluxing ethanol
  7. filtrationthe resulting mixture filtered hot

Sources & evidence

ORD record
ord-035405be72ad4e4fb64b46bd999c12ed
Source dataset
uspto-grants-1988_11
Patent number
US04787931

Reaction notes

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