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N-Phenylglycine

N-Phenylglycine is an organic compound with the formula C<sub>6</sub>H<sub>5</sub>NHCH<sub>2</sub>CO<sub>2</sub>H. This white solid achieved fame as the industrial precursor to indigo dye. It is a non-proteinogenic alpha amino acid related to sarcosine, but with an N-phenyl group in place of N-methyl.

Preparation

It is prepared by the Strecker reaction involving the reaction of formaldehyde, hydrogen cyanide, and aniline. The resulting amino nitrile is hydrolyzed to give the carboxylic acid.

See also

  • Phenylglycine, an isomer with the formula C<sub>6</sub>H<sub>5</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H.

References