Schotten-Baumann amide
Additional step: activation of carboxy group (COOH into COCl)
SMARTS: [C;$(C=O):1][OH1].[N;$(N[#6]);!$(N=*);!$([N-]);!$(N#*);!$([ND3]);!$([ND4]);!$(N[O,N]);!$(N[C,S]=[S,O,N]):2]>>[C:1][N+0:2]
Conditions
Reactant 1: carboxylic acid.
Reactant 2: primary or secondary amine.
R1, R2: aryl, alkyl. R3: H, alky, aryl.
References
Schotten, C. Ber. Dtsch. Chem. Ges. 1884, 17, 2544–2547.
Baumann, E. Ber. Dtsch. Chem. Ges. 1886, 19, 3218–3222.
Other sources
Organic chemistry
Wikipedia