Nitric Acid → HCID 44550991, compound
Reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:4]1.[N+:25]([O-])([OH:27])=[O:26]>C(Cl)Cl>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[C:8]([N+:25]([O-:27])=[O:26])=[CH:7][C:6]=2[N:5]([C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 128 (300 mg, 0.84 mmol) in CH2Cl2 (20 mL) was treated with filming HNO3 (2 mL) for 30 min at room temperature, then quenched with ice and extracted with CH2Cl2 (3×50 ml). The extracts were dried and concentrated under reduced pressure, and the residue was chromatographed on silica gel. Elution with EtOAc/petroleum ether/methanol (from 5:1:0 to 9:0:1) gave 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carboxamide (129) (150 mg, 45%) as yellow solid: mp 272-277° C. (EtOAc/petroleum ether); 1H NMR [(CD3)2SO] δ 8.78 (s, 1H), 8.30 (dd, J=8.4, 1.1 Hz, 1H), 8.24 (s, 1H), 7.91 (dd, J=7.1, 1.0 Hz, 1H), 7.80 (dd, J=8.4, 7.1 Hz, 11), 7.57 (s, 1H), 4.69-4.61 (m, 2H), 4.52-4.47 (m, 1H), 4.21-4.15 (m, 1H), 4.13-4.07 (m, 1H); 13C NMR δ 169.3, 153.6 (q, JC-F 37.8 Hz), 148.1, 138.6, 133.4, 132.4, 130.1, 128.7, 127.9, 126.1, 119.3, 115.6 (q, JC-F 288 Hz), 114.4, 52.7, 47.5, 41.2. Anal. (C16H11ClF3N3O4) C, H, N, Cl.