Ammonia → HCID 14451767, compound

Participants

Reaction Conditions

Reaction Steps

The methyl 4-aminophenylbutyrate hydrogensulfate, FW=291.11, 10.0 grams, 34.35 mmol, 1 eq) was dissolved in 20 ml of solution of 20% w/w aqueous NaCl (16 ml H2O and 4 grams of NaCl). To this solution aqueous ammonia (10 eq, 350 mmol, 14.8 molar solution, 24 ml) containing dissolved NaCl (4 grams) was added maintaining temperature 15-20° C. The mixture was stirred for 16 hours at RT. After that the mixture was cooled to 0-5° C. and held at this temperature for at least one hour. The resultant crystalline product was isolated by filtration. Washed with cold water (2 times for 10 ml) and dried under vacuum at 50° C. giving 5.5 g (90% yield) of 4-aminophenylbutyramide. C10H14N2O (MW 178.11); 1H NMR (500 MHz, DMSO-d6) δ: 7.23 ppm (br. s, 1H); 6.83 ppm (d, 2H, J=8.30 Hz); 6.68 ppm (br. s, 1H); 6.49 ppm (d, 2H, J=8.35 Hz); 4.80 ppm (br. s, 2H); 2.38 ppm (t, 2H, J=7.60 Hz); 2.03 ppm (t, 2H, J=7.53 Hz); 1.69 ppm (pentet, 2H, J=7.57 Hz).

Provenance & Evidence