4-Aminophenylacetic acid → HCID 67021355, compound

Participants

Reaction Steps

A mixture of 4-chloro-3-nitropyridine (0.500 g, 3.06 mmol) (LANCASTER) and (4-aminophenyl)-acetic acid (0.467 g 3.06 mmol) (Aldrich) in MeOH/dioxane (10 mL, 1/1 v/v) is stirred and refluxed for 6 h. The mixture is allowed to cool to rt and concentrated in vacuo to afford crude [4-(3-nitro-pyridin-4-ylamino)-phenyl]-acetic acid methyl ester. A suspension of the crude ester (0.569 g) and Raney Ni (˜0.140 g) in MeOH (15 mL) is stirred for 21 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of Celite and concentrated. Trituration of the residue in CH2Cl2 affords the title compound as a beige solid: ES-MS: 258.0 [M+H]+; single peak at tR=2.54 min (System 1).

Provenance & Evidence