Diethyl oxalacetate → HCID 58648590, compound

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].C(O[C:13](=[O:22])[CH2:14][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=O)C.CC#N.O>CO>[CH2:20]([O:19][C:17](=[O:18])[CH:15]=[C:14]1[C:13](=[O:22])[N:2]([CH3:1])[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:9]1)[CH3:21]

Participants

Procedure

To a solution of N-methyl-1,2-phenylenediamine (6.1 g, 4.99 mmol) in MeOH (50 mL) was added in portion of oxalacetic acid diethyl ester (9.9 g, 5.26 mmol). The mixture was then stirred at rt for 1 h. The precipitate was collected via filtration and was washed with small amount of methanol to yield a pale brownish solid as the pure product: 1H NMR (DMSO-d6) δ=11.1 (bs, 1H), 7.45-7.42 (m, 1H), 7.32-7.29 (m, 1H), 7.15-7.10 (m, 2H), 5.53 (s, 1H), 4.14 (q, J=9.0 Hz, 2H), 3.51 (s, 3H), 1.23 (t, J=9.0 Hz, 3H); HPLC (CH3CN—H2O-0.1% TFA) (short column): Rt=3.91 min.