Stannous Chloride → HCID 21710146, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4.0 grams (0.018 mole) of 4-amino-7-chloro-2-(1-methylethyl)isoindolin-1-one in 40 mL of concentrated hydrochloric acid was cooled in an ice-water bath, and a solution of 1.2 grams (0.018 mole) of sodium nitrite in 20 mL of water was added dropwise while maintaining the reaction mixture temperature under 5° C. Upon completion of addition, the reaction mixture was stirred for about 45 minutes, then a solution of 8.8 grams (0.039 mole) of tin(II) chloride in 20 mL of concentrated hydrochloric acid was added dropwise while still maintaining the reaction mixture temperature under 5° C. After this time the reaction mixture was stirred for about one hour at 5° C., then it was filtered to collect, after drying, 4.6 grams of subject compound, mp 186° C., dec. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence