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

HRID 245128Notes

Reaction equation

HRID 245128 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

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 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.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with water
  5. additionacidified by addition of aqueous hydrochloric acid (concentrated)
  6. customThe precipitate was isolated by filtration
  7. customdried at 80° C. for 16 hours

Sources & evidence

ORD record
ord-1f34e12f377148f9ac4689c55bdb932d
Source dataset
uspto-grants-2014_02
Patent number
US08658698B2

Reaction notes

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