Ethanolamine → 2-[(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)amino]ethanol
Reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[N:7]=[N+:8]([O-:19])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH2:16]3)=[CH:12][C:10]=2[N:11]=1>COCCOC>[O-:19][N+:8]1[C:9]2[CH:18]=[C:17]3[C:13](=[CH:12][C:10]=2[N:11]=[C:6]([NH:1][CH2:2][CH2:3][OH:4])[N:7]=1)[CH2:14][CH2:15][CH2:16]3Participants
4
Procedure
2-Aminoethanol (1.80 mL, 30.0 mmol) was added to a stirred solution of chloride 21 (2.21 g, 10.0 mmol) in DME (100 mL) and the solution stirred at reflux temperature for 90 min. The solvent was evaporated and the residue stirred with water (150 mL) at 20° C. for 30 min. The solid was filtered, washed with water several times and dried to give alcohol 24 (2.44 g, 99%) as an orange solid: mp (DME/water) 222-224° C.; 1H NMR [(CD3)2SO] δ 7.92 (s, 1H, H-9), 7.54 (br t, J=6.0 Hz, 1H, NH), 7.36 (s, 1H, H-5), 4.68 (t, J=6.0 Hz, 1H, OH)), 3.56 (q, J=6.0 Hz, 2H, CH2O), 3.40 (q, J=6.0 Hz, 2H, CH2N), 2.89-3.00 (m, 4H, H-6, H-8), 2.00-2.08 (m, 2H, H-7); 13C NMR [(CD3)2SO] δ 158.7, 154.0 148.0, 142.3, 128.8, 120.0, 113.9, 59.3, 43.2, 32.4, 31.6, 25.2. Anal. calcd for C12H14N4O2: C, 58.5; H, 5.7; N, 22.8. Found: C, 58.8; H, 5.9; N, 22.9%.