2-Methylbenzylamine → HCID 67520987, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl dimethoxyacetate (2.11 g, 15.6 mmol) and o-xylylamine (1.90 g, 15.4 mmol) in a 15 mL sealed tube was stirred at 55° C. for 11 d. The reaction solution was dissolved in EtOAc (≈60 mL) and washed with dil. HCl, water, sat. NaHCO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight to give the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3): δ=7.25-7.16 (m, 4H), 6.69 (brs, 1H), 4.75 (s, 1H), 4.48 (d, J=5.6 Hz, 2H), 3.40 (s, 6H), 2.33 (s, 3H). MS(ES+): m/z=246.07 (83) [MNa+], 224.11 (100) [MH+], 192.14 (60) [MH+-MeOH], 160.10 (95) [MH+-2 MeOH]. HPLC: tR=2.82 min (polar—5 min, ZQ3).

Provenance & Evidence