Synthesis of N-Phenylglycine

Preparation of N-Phenylglycine

Preparation of N-Phenylglycine

Preparation of N-Phenylglycine

Chloroacetic acid (19 g.) is exactly neutralised in the cold with 100 c.c. of 2 N-sodium hydroxide solution, 18,6 g of aniline are added, and the mixture is boiled for a short time under reflux until the aniline has reacted and dissolved. On cooling, the phenylglycine separates as an oil which soon crystallises when rubbed. The crystalline material is kept cool in ice for some time, collected at the pump, and washed with a little ice-cold water. Yield 22-24 g. of dry substance. In order to prepare the potassium or salt, 20 g. of phenylglycine are made exactly neutral to phenolphthalein with 2 N-potassium hydroxide (or sodium hydroxide) solution (about 70 c.c. are required), and the clear solution is then evaporated to dryness on the water bath.

Reference: Laboratory methods of organic chemistry, L. Gattermann, The Macmillan Company New York, 1937; p. 369-372

IUPAC Name

2-anilinoacetic acid

InChI

InChI=1S/C8H9NO2/c10-8(11)6-9-7-4-2-1-3-5-7/h1-5,9H,6H2,(H,10,11)

InChI Key

NPKSPKHJBVJUKB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)NCC(=O)O

MeSH Synonyms

N-phenylglycine, N-phenylglycine, potassium salt, N-phenylglycine, sodium salt

Depositor-Supplied Synonyms

N-Phenylglycine, Anilinoacetic acid, 103-01-5, 2-(phenylamino)acetic acid, N-phenyl glycine, 2-anilinoacetic acid, Glycine, N-phenyl-, N-Phenylaminoacetic acid, CHEBI:55477, (Phenylamino)acetic acid, NPKSPKHJBVJUKB-UHFFFAOYSA-N, MFCD00014009, SBB028637, phenylglycin, Glycine, phenyl-, Ph-Gly-OH, Phenylaminoacetic acid, Epitope ID:122700, AC1L24GE, UNII-37YJW036TP, SCHEMBL41828, BIDD:GT0243, N-alpha-Aminophenylacetic acid, 330469_ALDRICH, 37YJW036TP, Jsp000319, CHEMBL3306206, DTXSID2047016, CTK3H2589, ZINC389534, ACMC-209844, ALBB-000236, 19525-59-8 (potassium salt), EINECS 203-070-2, ANW-14786, BBL012003, STK397549, 10265-69-7 (hydrochloride salt), AKOS000101581, AM81798, MCULE-4813130378, RP21484, TRA0084741, VZ33023, AC-13995, AJ-20818, AK-45498, AM038681, KB-50359, KB-58777, M777, OR195314, AB0015382, AI3-09070, KB-104832, ST2416223, TR-000699, BB 0240669, FT-0653744, FT-0695168, P0180, ST50632573, 3630-EP2272972A1, 3630-EP2272973A1, 3630-EP2275102A1, 3630-EP2277867A2, 3630-EP2277872A1, 3630-EP2280003A2, 3630-EP2284170A1, 3630-EP2289868A1, 3630-EP2292595A1, 3630-EP2295055A2, 3630-EP2295410A1, 3630-EP2298778A1, 3630-EP2301939A1, 3630-EP2311453A1, 3630-EP2311835A1, 3630-EP2316974A1, 3630-EP2374786A1, X-2034, AB01331192-02, I01-0671, I01-6973, W-108859, 91981-32-7

Removed Synonyms

L-Phenylglycine, Phenylglycine, N-Benzylglycine, DL-Phenylglycine, H-DL-Phg-OH, C8H9NO2, MolPort-000-886-233, CID66025, RTR-000699, A1841, A7673, NPG, 2935-35-5, 108-36-1

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