Malonic Acid → 3-Methyl-2-nitrocinnamic acid
Reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:14][C:15]([OH:17])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Methyl-2-nitrobenzaldehyde, prepared according to Berichte, 47, 406, is reacted with malonic acid in pyridine with the addition of piperidine to give 3-methyl-2-nitrocinnamic acid; yield 64% of theory; m.p. 230°-235° C., after recrystallisation from methanol. After hydrogenation thereof in aqueous sodium hydroxide solution in the presence of palladium catalyst, 2 mole of acetic anhydride are added thereto and the reaction product is purified on an Amberlite IR-120 column (H+ form). There is thus obtained, in a yield of 75% of theory, 3-(2-acetylamino-3-methyl-phenyl)-propionic acid; m.p. 110° C. sinters, 117°-120° C. This is then reacted with phosphorous acid/phosphorus trichloride analogously to Example 16.
Sources & evidence
- ORD record
- ord-37f1937066db4ac1af09679a722cdd6a
- Source dataset
- uspto-grants-1988_01
- Patent number
- US04719203
Reaction notes
Loading…