Dimethylamine → Ethyl N-(3,4-dichlorobenzyl)-4-dimethylaminomethyl-5-hydroxyindole-2-carboxylate

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:25][N:26]([CH3:28])[CH3:27])[C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

参加物

実験手順

To a stirred solution of ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate (2.1 g) in ethanol (50 ml) was added successively aqueous dimetylamine (40%, 0.5 ml) and aqueous formaldehyde (0.5 ml). The solution was allowed to stand overnight and the resulting crystals filtered and dried in vacuo to give the product as pale yellow crystals (1.7 g, 70%); NMR δ(CD3SOCD3) 1.24 (t, 3H), 2.23 (s, 6H), 3.81 (s, 2H), 4.24 (q, 2H), 5.75 (s, 2H), 6.82 (d, 1H), 6.90 (dd, 1H), 7.30 (m, 3H), 7.50 (d, 1H); M/z (+) 423.421 (MH−), 378, 376.