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ChemicalBook CAS DataBase List 7,8-Dibromo-2-chloro-9-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline
1609452-31-4

7,8-Dibromo-2-chloro-9-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline synthesis

3synthesis methods
2-CHLORO-9-METHYL-5,6-DIHYDRO-4H-IMIDAZO[4,5,1-IJ]QUINOLINE

1609453-56-6
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7,8-Dibromo-2-chloro-9-methyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

1609452-31-4
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Yield:1609452-31-4 90%

Reaction Conditions:

with N-Bromosuccinimide in acetonitrile at 0 - 20; for 49.5 h;

Steps:

7, 8-dibromo-2-chloro-9-methyl-5 ,6-dihydro-4H-imidazo [4,5,1 -]quino line (Method2A)

7, 8-dibromo-2-chloro-9-methyl-5 ,6-dihydro-4H-imidazo [4,5,1 -]quino line (Method2A) A 2-chloro-9-methyl-5,6-dihydro-4H-imidazo[4,5,1-]quinoline (11.7 g, 56 mmol)(Method 14A) was dissolved in acetonitrile (250 mL) cooled to 0°C and next Nbromosuccinimide (50.0 g, 282 mmol) was added portionwise over lh. The reaction mixture was stirred at 0°C for 30minutes then at room temperature for 48 hours. The solvent was evaporated under reduced pressure and residue was dissolved in dichloromethane and washed with saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to gave 18.6g of 7,8-dibromo-2-chloro-9-methyl-5,6- dihydro-4H-imidazo[4,5,1-]quinoline; yield 90%; LC-MS (m/z) 364.8 (M+1). 1H NMR (600 MHz, DMSO) ? 4.12 (t, 2H, CH2), 2,88 (t, 2H, CH2), 2.57 (s, 3H, CH3), 2.22-2.18 (m, 2H, CH2).

References:

WO2014/72435,2014,A1 Location in patent:Page/Page column 79