Ethanol → N-butyl-3-methyl-terephthalamic acid

Reaction equation

[OH-:1].[Na+].[CH2:3]([NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13]C(C#N)=[CH:11][C:10]=1[CH3:17])[CH2:4][CH2:5][CH3:6].[CH2:19]([OH:21])[CH3:20]>>[CH2:3]([NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:20]([C:19]([OH:1])=[O:21])=[CH:11][C:10]=1[CH3:17])[CH2:4][CH2:5][CH3:6]

Participants

Reactant 3

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 67025299N-butyl-4-cyano-2-methyl-benzamide

Product 1

HCID 67025400N-butyl-3-methyl-terephthalamic acid

Procedure

Sodium hydroxide (4.080 g, 102 mmol) was added at ambient temperature to a solution of N-butyl-4-cyano-2-methyl-benzamide (0.919 g, 4.25 mmol) (Example I2) in ethanol (10 ml). The reaction mixture was heated to reflux for 3 hours. The reaction mixture was cooled to ambient temperature and concentrated. The residue was diluted with water and acidified by addition of aqueous hydrochloric acid (concentrated). The precipitate was isolated by filtration and dried at 80° C. for 16 hours to give N-butyl-3-methyl-terephthalamic acid, which was used without further purification. 1H-NMR (DMSO-d6, 400 MHz): 0.97 (3H, t), 1.42 (2H, m), 1.62 (2H, m), 2.48 (3H, s), 3.47 (2H, q), 5.73 (1H, s), 7.45 (1H, d), 7.92 (2H, d), 7.5 (1H, s) ppm.