3-(2-aminoethyl)benzoic acid → Benzoic Acid
Reaction equation
NCC[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].C([O-])(=O)C.[Na+].C(N1C=CC=C(C(Cl)=O)C1=O)C1C=CC=CC=1>CC(C)=O>[C:7]([OH:9])(=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:4][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
20 ml of acetone are added to 16 ml of an about 1 molar solution of 3-(2-aminoethyl)-benzoic acid containing the corresponding amount of sodium acetate, and 3.7 g of 1-benzyl-1,2-dihydro-2-oxo-nicotinic acid chloride (prepared from 1-benzyl-1,2-dihydro-2-oxo-nicotinic acid and thionyl chloride) are added with agitation and cooling. Agitation is then continued for 1 hour at room temperature, the acetone is removed under reduced pressure, and dilute hydrochloric acid is added to the residue. The precipitated product is suction-filtered, reprecipitated from dilute ammonia, and recrystallized from dilute methanol. The 4-(2-<1-benzyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzoic acid so obtained has a melting point of 150°-152° C. and of 171°-173° C.