Sodium Bicarbonate → HCID 20291882, compound

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Reaction Steps

4-(3-Nitrophthalimidyl)-aniline, used in the above example, can be prepared as follows: 48.3 g (0.25 mol) of 3-nitrophthalic anhydride and 37.5 g (0.25 mol) of 4-aminoacetanilide in 500 ml of acetic acid are refluxed for 8 hours and are then cooled. The crystals which have separated out are filtered off with suction, washed with 150 ml of ethanol and dried for 24 hours at 80° C./30 mm Hg. 65 g (80% of theory) of 4-(3-nitrophthalimidyl)-acetanilide are obtained; melting point 255° C. 65 g (0.2 mol) of 4-(3-nitrophthalimidyl)-acetanilide are heated with a mixture of 400 ml of dioxan and 200 ml of concentrated hydrochloric acid for 3 hours at 90° C. and the whole is then left to stand for 24 hours at 25° C. The crystals which have separated out are filtered off with suction and washed with 100 ml of methanol. 45 g (70% of theory) of crude 4-(3-nitrophthalimidyl)-aniline hydrochloride are obtained. 45 g (0.14 mol) of this hydrochloride are mixed with 100 ml of water and 200 ml of a saturated sodium bicarbonate solution are added dropwise at 5° C. After one hour, the resulting fine precipitate is filtered off with suction, washed three times with 50 ml of water and dried for 24 hours at 25° C./1 mm Hg. 21 g (54% of theory) of 4-(3-nitrophthalimidyl)-aniline are obtained; melting point 177° C. IR spectrum (KBr): 1790 and 1725 cm-1 (CO--N--CO); 1540 and 1360 cm-1 (NO2).

Provenance & Evidence