Nitric Acid → HCID 44550859, 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]#[N:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:4]1.[N+:24]([O-])([OH:26])=[O:25]>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]#[N:17])[C:9]=3[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])[CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 126 (60 mg, 0.18 mmol) in CH2Cl2 (10 mL) was treated with fuming HNO3 (1.5 mL) and stirred for 30 min at room temperature. The reaction was quenched with ice and extracted with CH2Cl2 (3×50 ml). The extracts were dried and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with EtOAc/petroleum ether (from 1:4 to 1:1), to give 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carbonitrile (127) (28 mg, 41%) as a brown solid: mp EtOAc/petroleum ether) 201-205° C. (dec.); 1H NMR [(CD3)2SO] δ 8.87 (s, 1H), 8.63 (dd, J=8.5, 1.1 Hz, 1H), 8.40 (dd, J=7.3, 1.0 Hz, 1H), 7.93 (dd, J=8.5, 7.3 Hz, 1H), 4.73-4.61 (m, 2H), 4.55-4.49 (m, 1H), 4.22-4.15 (m, 1H), 4.12-4.07 (m, 1H); 13C NMR δ 153.8 (q, JC-F 37.6 Hz), 146.8, 139.8, 137.7, 132.6, 130.3, 129.4, 128.3, 118.7, 115.4 (q, JC-F 288 Hz), 115.1, 114.8, 105.4, 52.7, 47.4, 41.1. Anal. (C16H9ClF3N3O3) C, H, N.