Ammonium Hydroxide → [2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

2,6-Dichloro-4-trifluoromethylphenylaniline (4.3 g) (described in U.S. Pat. No. 3,850,955) was dissolved, with stirring, in glacial acetic acid (23 ml). A solution of sodium nitrite (1.5 g) in concentrated sulphuric acid (11 ml) was then added at 55°-60° C. The solution thus obtained was cooled to 0°-5° C. and a solution of stannous chloride (16.4 g) in concentrated hydrochloric acid (14 ml) was added with vigorous stirring. A cream-coloured solid precipitated. The mixture was filtered and the solid obtained was added to a mixture of aqueous ammonium hydroxide solution and ice. The mixture thus obtained was extracted with diethyl ether (6×500 ml) and the combined ethereal extracts were dried over sodium sulphate, filtered and evaporated to dryness to give 2,6-dichloro-4-trifluoromethylphenylhydrazine (3.7 g), m.p. 54°-56° C., in the form of a colourless crystalline solid.

1. dissolution3,850,955) was dissolved
2. customThe solution thus obtained
3. temperaturewas cooled to 0°-5° C.
4. customA cream-coloured solid precipitated
5. filtrationThe mixture was filtered
6. customthe solid obtained
7. customThe mixture thus obtained
8. extractionwas extracted with diethyl ether (6×500 ml)
9. dry with materialthe combined ethereal extracts were dried over sodium sulphate
10. filtrationfiltered
11. customevaporated to dryness

ORD record

ord-35024cf3d4f64b6eabe9d99a59fdfb0a

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04541963