4-Chloro-6,7-dimethoxy-3-nitroquinoline → HCID 619079, compound

Participants

Reaction Conditions

Reaction Steps

Zn(CH3)2 (1.2 M in toluene, 15.35 ml, 18.43 mmol) and Pd(dppf)Cl2 (2.28 g, 2.92 mmol) are added to a solution of 4-chloro-6,7-dimethoxy-3-nitroquinoline (7.5 g, 27.92 mmol) in water- and oxygen-free dioxane (200 ml, pre-treatment: nitrogen gas passed through for 30 min). The reaction mixture is heated at 80° C. for 8 h, giving a solution. After cooling to room temperature, water (65 ml) is slowly added, and the mixture is extracted with ethyl acetate (60 ml). After separation, the organic phase is washed with a little hydrochloric acid (1.0 M, 5 ml). The aqueous phase is extracted three times with ethyl acetate (60 ml each time). The combined organic phases are dried over Na2SO4, filtered with suction and evaporated to dryness in vacuo. The residue is purified by chromatography over flash silica gel (solvent cyclohexane/ethyl acetate 2:1, parts by volume), giving 6,7-dimethoxy-4-methyl-3-nitroquinoline (5.82 g, 23.44 mmol) as a solid. MS: 249.0 (M+H+), TLC (HPTLC): Rf=0.45 (cyclohexane/ethyl acetate 1:1, parts by volume).

Provenance & Evidence