Chloroform → (4-Chloro-5-(difluoromethoxy)-2-fluorophenyl)hydrazine

HRID 2309318Notes

Reaction equation

HRID 2309318 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH:10]([F:12])[F:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[N:14]([O-])=O.[Na+].[OH-].[Na+].C(Cl)(Cl)Cl>O.Cl>[Cl:1][C:2]1[C:8]([O:9][CH:10]([F:11])[F:12])=[CH:7][C:5]([NH:6][NH2:14])=[C:4]([F:13])[CH:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 1847674-Chloro-5-(difluoromethoxy)-2-fluoroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 184768(4-Chloro-5-(difluoromethoxy)-2-fluorophenyl)hydrazineYield 89.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 13.3 g of 4-chloro-2-fluoro-5-difluoromethoxyaniline XIII-1 and 106 ml of hydrochloric acid was stirred at 0° C. A solution of 4.76 g of sodium nitrite in 35.4 ml of water was dropwise added in 10 minutes to the mixture, which was stirred at 0° to 5° C. for an hour. A solution of 35.4 g of stannous chloride dihydrate in 35.4 ml of hydrochloric acid was dropwise added in 15 minutes to the mixture, which was stirred at 0° to 5° C. for 2 hours. The reaction mixture was basified with 10% aqueous sodium hydroxide and shaken with chloroform. The chloroform layer was dried and concentrated, and 12.7 g of the titled compound XIV-1 thus obtained was used for the subsequent reaction without purification.

Workup

  1. stirringwas stirred at 0° to 5° C. for an hour
  2. stirringwas stirred at 0° to 5° C. for 2 hours
  3. dry with materialThe chloroform layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22e4abc191404b94929d86defa736457
Source dataset
uspto-grants-1987_09
Patent number
US04695312

Reaction notes

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