Ethanol → 8-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid ethyl ester
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4[CH:12]=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=4[CH2:17][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[CH2:26](O)[CH3:27]>>[CH2:26]([O:19][C:18]([C:15]1[C:16]2[CH2:17][C:5]3[C:4]4[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:8]=4[NH:7][C:6]=3[C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:20])[CH3:27]Participants
4
Procedure
The product of Example 20 was converted to its ethyl ester by treatment with sulfuric acid in ethanol to give the title compound as an off-white solid: mp 202-204° C.; 1H NMR (DMSO-d6,): δ 1.39 (t, 3H), 4.00 (s, 2H), 4.38 (q, 2H), 7.11 (d, 1H), 7.48 (d, 1H), 7.52 (t, 1H), 7.67 (s, 1H), 7.79-7.84 (m, 2H), 11.86 (s, 1H); MS [EI, m/z]: 311 [M]+.