Sodium Hydroxide → 4-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)phenylhydrazine

HRID 1722923Notes

Reaction equation

HRID 1722923 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH2:10][CH:11]2[CH2:13][C:12]2([F:15])[F:14])=[CH:7][C:5]([NH2:6])=[C:4]([F:16])[CH:3]=1.[N:17]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.Cl>[Cl:1][C:2]1[C:8]([O:9][CH2:10][CH:11]2[CH2:13][C:12]2([F:14])[F:15])=[CH:7][C:5]([NH:6][NH2:17])=[C:4]([F:16])[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 141294324-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 141294354-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)phenylhydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

29.3 g 4-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)aniline was treated first with 45 ml half concentrated hydrochloric acid and then with 273 ml concentrated hydrochloric acid. It was then cooled to -10° C. and treated dropwise with a solution of 8.3 g sodium nitrite in 17 ml water at a such rate that the temperature of the reaction mixture did not rise above -5° C. It was stirred for 3 hours at -5° C. and the at -15° C., a solution of tin (II) chloride dihydrate in 34 ml concentrated hydrochloric acid added dropwise at such a rate that the temperature of the reaction mixture did not exceed -10° C. It was warmed at room temperature overnight. For the work-up, it was cooled to 0° C. and slowly neutralised with with 430 ml 32% caustic soda solution. The precipitated tin hydroxide slurry was separated by filtration through Celite and the filter cake washed with ether and the aqueous mother liquor extracted with ether. The combined organic phases were dried over magnesium sulphate and the solvent removed.

Workup

  1. customdid not rise above -5° C
  2. customdid not exceed -10° C
  3. temperatureIt was warmed at room temperature overnight
  4. customThe precipitated tin hydroxide slurry was separated by filtration through Celite
  5. washthe filter cake washed with ether
  6. extractionthe aqueous mother liquor extracted with ether
  7. dry with materialThe combined organic phases were dried over magnesium sulphate
  8. customthe solvent removed

Sources & evidence

ORD record
ord-a929472749ed4e4ab58530842fd7faab
Source dataset
uspto-grants-1989_08
Patent number
US04859230

Reaction notes

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