ChemicalBook CAS DataBase List 7-BROMO-2-METHYLQUINOLINE

7-BROMO-2-METHYLQUINOLINE synthesis

6synthesis methods

Product Name:7-BROMO-2-METHYLQUINOLINE
CAS Number:4965-34-8
Molecular formula:C10H8BrN
Molecular Weight:222.08

591-19-5
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123-63-7 Synthesis

123-63-7
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4965-34-8
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$65.00/50mg

Yield: 46%

Reaction Conditions:

Stage #1:m-Bromoaniline;paracetaldehyde with hydrogenchloride in water at 0 - 20; for 4 h;Reflux;Doebner-Miller Synthesis;
Stage #2: with sodium hydroxide in water at 0;

Steps:

Doebner Miller synthesis: 3-Bromoaniline (10 mL, 92 mmol) was added to a solution of 37 % HCl at 0 °C (200 mL). Paraldehyde (11 mL, 0.8 mol, 9 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, and then heated to reflux temperature for 3 hours. After cooling to 0 °C, a saturated aquous solution of sodium hydroxide (200 mL) was slowly added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over MgSO₄, and concentrated under reduced pressure. The crude product was obtained as a mixture of 5-bromoquinaldine and 7-bromoquinaldine that were separated by column chromatography (SiO₂, cyclohexane-AcOEt 9:1). The 7-bromoquinaldine regioisomer was obtained as a sand yellow solid (9,3 g, 46 %). Molecular formula: C₁₀H₈BrN. Molecular weight: 222.08 g.mol^-1. IR (film): 1610, 1494, 1264, 841, 736 cm^-1. T_fusion: 57 °C. ¹H NMR: δ 8.09 (s, 1H, H₈), 7.80 (d, J = 8.2 Hz, 1H, H₄), 7.39 (m, 2H, H₅ et H₇), 7.12 (d, J = 8.2 Hz, 1H, H₃), 2.61 (s, 3H, H₉). ¹³C NMR: δ 160.3 (s, C₂), 148.6 (s, C_8a), 136.2 (s, C₄), 131.2 (s, C₈), 129.4 (s, C₅), 128.9 (s, C₆), 125.3 (s, C_4a), 123.7 (s, C₇), 122.6 (s, C₃), 25.7 (s, C₉).