4-Cyanophenylacetic acid

Off-white crystals

To a suspension of 4-amino-phenylacetic acid (18.2 g, 120.4 mmol), concentrated HC1 (24.7 mL) and water (90 mL) warmed by a 40 °C water bath, acetic acid (13 mL) was added. This solution was cooled to 0-5 °C by an ice- water bath and a solution of sodium nitrite (9 g, 130.4 mmol) in water (32 mL) was added dropwise within 20 minutes. The orange solution was stirred for another 25 minutes at 0- 5 °C and then it was added by a glass pipette (10 mL) slowly to a solution of sodium cyanide (29.5 g, 602 mmol), copper cyanide (21.6 g, 241 mmol) and water (280 mL) at 4- 5 °C within 40 minutes. The black suspension was kept stirring at 4°C for 1 hr and room temperature for 2 hr. The suspension was filtrated through celite and the precipitate was washed with EtOAc (50 mL, twice). The filtration was extracted with EtOAc three times. The combined organic layers were dried over anhydrous NA2S04 and the solvent was concentrated under reduced pressure. The residue was applied to a column CHROMATOGRAPHY (SIO2, 20percent MEOH in EtOAc) to give 44 (15.3 g, 78.9percent) as yellow solid.Preparative Example 9B; A solution of commercially available 4-bromophenyl-acetic acid (1.5 g), Zn(CN)

Molecular Weight:161.16
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:61.1
Heavy Atom Count:12
Complexity:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes