Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)- → (4-Chloro-2-fluoro-5-propan-2-yloxyphenyl)hydrazine

HRID 1164713Notes

Reaction equation

[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[N:14]([O-])=O.[Na+]>O.Cl>[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:7][C:5]([NH:6][NH2:14])=[C:4]([F:13])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 11.0 g (0.054 mole) of 4-chloro-2-fluoro-5-(1-methylethoxy)aniline and 50 mL of concentrated hydrochloric acid was cooled to 0° C. and a solution of 3.7 g (0.054 mole) of sodium nitrite in 15 mL of water was added dropwise. The reaction mixture temperature was not allowed to rise above 6° C. during the addition. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes and a solution of 26.8 g (0.12 mole) of stannous chloride in 30 mL of concentrated hydrochloric acid was added dropwise. Upon completion of addition the reaction mixture was stirred at 0° C. for one hour then was filtered to collect a solid precipitate. The solid was slurried in 100 mL of aqueous 25% sodium hydroxide and collected by filtration to give 11.0 g of 4-chloro-2-fluoro-5-(1-methylethoxy)phenylhydrazine.

Workup

additionto rise above 6° C. during the addition
additionUpon completion of addition the reaction mixture
additionUpon completion of addition the reaction mixture
stirringwas stirred at 0° C. for one hour
filtrationthen was filtered
customto collect a solid precipitate
filtrationcollected by filtration

Sources & evidence

ORD record: ord-663104f3afd64ebb87379d3e11fa4f25
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906284

Reaction notes

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