Sodium Hydroxide → [2-(Trifluoromethoxy)phenyl]hydrazine--hydrogen chloride (1/1)

A solution of o-trifluoromethoxyaniline (1.77 g, 10 mmol) in cold, concentrated HCl (11.6 mL) was diazotized at -5° C. (internal temperature) with a solution of NaNO2 (0.69 g, 10 mmol) in water (11 mL). After 15-20 minutes the mixture was treated portionwise with a cold (0° C.) solution of tin (II)chloride dihydrate (4.5 g, 20 mmol) in concentrated HCl (4 mL). Stirring was continued for another 3 hours with the ice bath warming to room temperature after one hour. The suspension was recooled, basified with 50% NaOH (to pH 14) and extracted with ether. The extracts were washed with 1N NaOH, water and brine, dried (MgSO4) and acidified with an excess of ethereal HCl. Removal of the solvent in vacuo yielded the title compound as an off-white solid (2 g, 88%). It was used without further purification.

1. customwas diazotized at -5° C.
2. extractionextracted with ether
3. washThe extracts were washed with 1N NaOH, water and brine
4. dry with materialdried (MgSO4)
5. customRemoval of the solvent in vacuo

ORD record

ord-2c420d57de85468c8dbd22b8966c184e

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960902