3-Iodoaniline → (3-Iodophenyl)hydrazine

To a stirred suspension of 3-iodoaniline (2 g, 9.13 mmol) in 37% hydrochloric acid (11 mL) at 0° C. was added a cold solution of sodium nitrite (0.66 g, 9.59 mmol) in water (3.2 mL). The resulting suspension was allowed to stir for 40 min. Then, a cold solution of tin(II) chloride dihydrate (6.18 g, 27.4 mmol) in 37% hydrochloric acid (4.3 mL) was added to the reaction mixture and stirred for another 40 min. The flask was then placed in the refrigerator for 12 h. The precipitate was isolated by filtration and washed with ice-cold brine (25 mL) followed by 2:1 petroleum ether/ether (25 mL) solution. The light pink solid was dried under vacuum for 2 h to give the title compound 61 (3.63 g, 94% yield) as the SnCl2 complex. LRMS (ESI): calc. 234.0; found 235.0 (MH)+ (compound 61 as the free hydrazine was previously reported in Recueil des Travaux Chimiques des Pays-Bas (1961), 80 1348-56).

1. stirringstirred for another 40 min
2. waitThe flask was then placed in the refrigerator for 12 h
3. customThe precipitate was isolated by filtration
4. washwashed with ice-cold brine (25 mL)
5. customThe light pink solid was dried under vacuum for 2 h

ORD record

ord-624af0203d354c7aa967960a5bf097bd

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338437B2