6-Bromo-2-methyl-4-quinolinol

POCl3 (5mL) was added to General procedure: The intermediates 6-bromo/6-chloro-4-hydrazinyl-2-methyl-quinoline 9a/9b, were prepared by following the reported procedures [1, 2]. To an equimolar quantity mixture of 4-chloro/bromo aniline 6a/6b (78.3 mmol) and ethyl acetoacetate (78.3 mmol), polyphosphoric acid (50g, 5 w/w) were added and the reaction mixture was heated with stirring for 2h at 150 C. After the completion of the reaction (as monitored by TLC), the reaction mixture was poured slowly into ice water with vigorous stirring. The precipitated solid was filtered and dried in vacuum oven to give the crude 6-bromo/6-chloro-2-methylquinolin-4-ol 7a/7b as yellow solid. The crude product was pure enough and was used for the next step without further purification. A mixture of compound 7a/7b (25.82 mmol) and phosphorous oxychloride (28 mL) was heated at 80 oC for 4 h. The reaction was monitored by TLC (Thin Layer Chromatography). After completion of the reaction, excess POCl3 was distilled off. The residue thus obtained was than stirred with ice water for 15 min. After this, the separated precipitates were filtered and dried to give corresponding chloro derivatives 8a/b. Further compound 8a/8b (32.0 mmol) and hydrazine hydrate (20 mL) in ethanol (20 mL) were heated under reflux at 90 C for 4 h. Completion of the reaction was monitored by TLC. The reaction mixture was concentrated and allowed to stand at room temperature to give solid. The solid product obtained was filtered, washed with water and dried. Yield: 72-75%. The 6-bromo/6-chloro-4-hydrazinyl-2-methylquinoline 9a/9b were confirmed with that of the reported ones [3].

Molecular Weight:238.08
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:236.97893
Monoisotopic Mass:236.97893
Topological Polar Surface Area:29.1
Heavy Atom Count:13
Complexity:262
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes