Aniline → HCID 178486196, compound

Reaction equation

[F:1][C:2]1[CH:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCCO)C.C(OCC)C>[ClH:20].[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH+:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[CH:3]=1

Participants

Procedure

A solution of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (530 mg, 1.79 mmol) and aniline (0.75 g, 8.06 mmol) in EtOCH2CH2OH (50 mL) was heated at 120° C. for 10 min. During this time the color of the reaction mixture changed from purple to yellow, and a yellow precipitate formed. After cooling, the reaction mixture was diluted with diethyl ether (100 mL) and the precipitate was collected, washed thoroughly with diethyl ether and dried, providing 555 mg (79.4%) of the title compound, mp 280° C. (sublimed); 1H NMR (DMSO-d6) δ 11.26 (s, NH), 10.62 (s, NH), 8.64 (d, J=8.0, 2H), 8.46 (d, J=9.2, 1H), 8.04 (t, J=8.0, 1H), 7.77-7.68 (m, 2H), 7.47-7.39 (m, 3H), 7.29-7.22 (m, 3H), 4.81 (s, 3H); 13C NMR (acetone-d6) δ 152.50 (d, J=259.5), 136.01, 132.03 (d, J=2.96), 130.95, 130.52, 127.76, 125.68, 123.12, 119.52, 117.72, 115.57, 115.32, 115.08, 113.86 (d, J=9.6), 113.37, 112.07 (d, J=9.7), 107.81, 106.57, 101.60 (d, J=26.2), 32.13; MS (EI, m/z) 340 (M+).