Lithium Hydroxide → HCID 67148381, compound

Participants

Reaction Steps

An aqueous solution of lithium hydroxide (0.5 M, 56 ml, 28 mmol) was added to a solution of methyl 4,5-dimethoxy-2-[(phenylacetamino)methyl]phenylacetate 6 (2 g, 5.6 mmol) in methanol (50 ml). The reaction mixture was stirred at ambient temperature for 12 hours, then neutralized with an aqueous solution of HCl (2N) and precipitation of the product was observed. Filtration gave the 4,5-dimethoxy-2-[(phenylacetamino)methyl]-phenylacetic acid 7 (1.5 g, 78%) in the form of a white powder. M.p.=186° C. 1H NMR ((CD3)2SO, 300 MHz) δ 8.40 (br s, 1H), 7.30-7.20 (m, 6H), 6.80 (s, 1H), 6.73 (s, 1H), 4.18 (d, J=5.6 Hz, 2H), 3.70 (s, 3H), 3.59 (s, 3H), 3.55 (s, 2H), 3.44 (s, 2H). 13C NMR ((CD3)2SO, 75 MHz) δ 172.8, 170.0, 147.4, 147.3, 136.6, 129.9, 129.0 (2C), 128.3 (2C), 126.4, 125.2, 114.6, 111.9, 55.6, 55.4, 42.5, 39.6, 37.5. Analysis calculated for C19H21NO5: C=66.46, H=6.16 and N=4.08. Analysis measured: C=66.52, H=5.92 and N=4.06.

Provenance & Evidence