[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[CH:2].[NH3:10]>>[C:6]1([CH3:9])[CH:7]=[CH:8][C:3]([C:1](=[NH:10])[CH3:2])=[CH:4][CH:5]=11-p-tolylethanimine was prepared by reacting 1-ethynyl-4-methylbenzene and excess ammonia in the presence of 5 mol % of catalyst E (110° C., 18 h). The yield was 60%. 1H NMR (600 MHz, C6D6) δ=2.17 (3H, s, CH3), 2.18 (3H, s, CH3), 7.07 (2H, d, J=7.9 Hz, CH), 7.72 (2H, d, J=7.9 Hz, CH); 13C NMR (150 MHz, C6D6) δ=21.3 (CH3), 25.7 (NCCH3), 127.3 (CHortho), 129.5 (CHmeta), 136.9 (Cq,ipso), 140.8 (Cq,paraCH3), 173.7 (C═NH); HRMS (ESI): 134.0968 [(MH)+, 134.0970 (C9H12N)].
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