Hydrochloric Acid → HCID 54718202, compound

Participants

Reaction Steps

The title compound was prepared as described in General Method 1 using 6.7 mmol of methyl acetoacetate, 7.3 mmol of NaH 60% dispersion in oil, 7.0 mmol of 1.6 M n-butyl lithium in hexane, 6.7 mmol of 2-(methylphenylamino)-1-phenylethanone and 40 mL of tetrahydrofuran. The reaction mixture was acidified to pH 7 with conc. HCl and then taken to pH 3 with acetic acid. The product was flash chromatographed using CH2Cl2 /MeOH (99/1) to give a solid (m.p. 152-153° C.). 1H NMR (CDCl3) δ 2.9 (d, 1 H), 3.05 (s, 3 H), 3.1 (d, 1 H), 3.2 (d, 1 H), 3.3 (d, 1 H), 3.7 (ABq, 2 H), 6.7-6.8 (m, 3 H), 7.2-7.3 (m, 2 H), 7.3-7.5 (m, 5 H).

Provenance & Evidence