ChemicalBook CAS DataBase List 3-CYANOPHENYLACETIC ACID

3-CYANOPHENYLACETIC ACID synthesis

4synthesis methods

Product Name:3-CYANOPHENYLACETIC ACID
CAS Number:1878-71-3
Molecular formula:C9H7NO2
Molecular Weight:161.16

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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Yield:-

Reaction Conditions:

with silver trifluoroacetate;triethylamine in tetrahydrofuran;water at 20 - 25;

Steps:

19
Reactant XII (2.0 g, 12 mmol) was dissolved in a mixture of THF (40 mL) and water (4 mL) and cooled to 25° C. A solution of silver trifluoroacetate (0.32 g, 1.45 mmol) in triethylamine (5.2 mL) was added in one portion and the reaction mixture was warmed to room temperature and stirred for 12 hours. The reaction mixture was concentrated and the residue was dissolved in 20% aqueous NaOH and washed with EtOAc (3×50 mL). The aqueous layer was acidified to pH 1 using 10% aqueous HCl and extracted with DCM (3×80 mL). The combined organic phases were dried over MgSO₄and concentrated. The residue was recrystallized from water and dried in a vacuum desiccator over P₂O₅/KOH to afford the reactant XIII (0.64 g, 34% yield) as an off-white solid (estimated purity 60%) which was characterized as follows:¹H NMR (400 MHz, DMSO-d6): δ 12.88 (1 H, br. s.), 7.69.7.77 (2 H, m), 7.62 (1 H, dt, J=7.5, 1.5 Hz), 7.53 (1 H, t, J=7.5 Hz) and 3.69 (2 H, s) ppm.

References:

NV reMYND US2010/197703, 2010, A1 Location in patent:Page/Page column 79-80; sheet 4