Benzoyl Peroxide → HCID 117727907, compound

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:42][CH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Procedure

To a refluxing solution of ethyl 2-methylquinoline-4-carboxylate (1.6 g, 7.60 mmol) in CCl4 (150 mL), benzoyl peroxide (186 mg, 0.767 mmol) was added followed by NBS (750 g, 4.23 mmol). After 1 h, a second batch of NBS (750 g, 4.23 mmol) was added and the refluxing was continued overnight. The reaction mixture was allowed to cool to rt and washed with satd. Na2CO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:100-2:3 EtOAc/heptanes) to obtain ethyl 2-(bromomethyl)quinoline-4-carboxylate. Mass Spectrum (LCMS, ESI pos.) Calcd. For C13H12BrNO2: 294.0 (M+H). Found 294.1.