Sodium Hydroxide → HCID 11427347, compound

HRID 1086750Notes

Reaction equation

HRID 1086750 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([Cl:21])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[OH-].[Na+]>C(O)C.Cl>[NH2:18][C:16]1[C:15]([Cl:21])=[CH:14][C:13]([F:22])=[C:12]([C:3]2[C:2]([Cl:1])=[C:6]([O:7][CH:8]([F:9])[F:10])[N:5]([CH3:11])[N:4]=2)[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 156723371-Methyl-5-difluoromethoxy-4-chloro-3-(2-fluoro-4-chloro-5-nitrophenyl)pyrazole

Product 1

HCID 11427347HCID 11427347, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To 4-chloro-3-(4-chloro-2-fluoro-5-nitrophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole (3.0 g, 8.5 mmoles) in a mixture of 15 ml ethanol and 15 ml conc. hydrochloric acid was added stannous chloride (7.70 g, 34 mmole) and the reduction was conducted under reflux for 8 hours. Then the product solution was poured into ice-cold water, the resulting mixture was made alkaline with 20% aqueous NaOH, and the objective product was extracted with ethyl acetate. Dehydration and concentration of the extract solution and purification of the residue by column chromatography gave the title compound (2.15 g), yield 78%.

Workup

  1. temperatureunder reflux for 8 hours
  2. additionThen the product solution was poured into ice-cold water
  3. extractionthe objective product was extracted with ethyl acetate
  4. customDehydration and concentration of the extract solution and purification of the residue by column chromatography

Sources & evidence

ORD record
ord-0c447ce7eac0468b86a8858b1bcc9c5e
Source dataset
uspto-grants-1991_07
Patent number
US05032165

Reaction notes

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