HCID 70622593, compound → HCID 70621330, compound

Participants

Reaction Steps

The solution of 416 g of N-(4-nitro-o-tolyl)-4-chlorophthalimide in 28 lt. of hot ethyl acetate is cooled slightly and transferred under nitrogen to 250 ml (or 460 g) of a suspension of Raney nickel, which has been washed 4 times with anhydrous ethanol and 1 time with ethyl acetate, and 12 lt of ethyl acetate are used for the rinse. The mixture is hydrogenated at 3.4 atm. and 30° for approximately 8 hours, and continued for 2 hours after the hydrogen uptake has ceased. It is filtered, the residue rinsed with 15 lt. of ethyl acetate and the filtrate concentrated to about 14 lt. It is cooled, filtered, and the filtrate reduced to approximately 1 1/2 lt to yield 2 crops of N-(4-amino-o-tolyl)-4-chlorophthalimide melting at 205°-207°; it is identical (but somewhat purer) than that obtained according to Example 2.

Provenance & Evidence