7-broMoquinolin-3-aMine

A suspension of intermediate 396 ( 14 g, 38.5 mmol) in ethanol ( 1 50 mL) was treated with NHA suspension of 2-(7-bromoquinolin-3-yl)isoindoline-l, 3-dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid was dissolved in warm ethanol and adsorbed onto silica gel. Purification of the solid by silica gel chromatography (50-100percent) ethyl acetate/hexanes) afforded the title compound (3.5 g, 56percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.83 (s, 2 H) 7.14 (d, J=2.53 Hz, 1 H) 7.49 (dd, J=8.84, 2.02 Hz, 1 H) 7.54 - 7.65 (m, 1 H) 7.94 (d, J=1.77 Hz, 1 H) 8.46 (d, J=2.78 Hz, 1 H).A suspension of 2-(7-bromoquinolin-3-yl)isoindoline-1 , 3-dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid was dissolved in warm ethanol and adsorbed onto silica gel. Purification of thesolid by silica gel chromatography (50-100percent ethyl acetate/hexanes) afforded the title compound (3.5 g, 56percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.83 (s, 2H) 7.14 (d, J=2.53 Hz, 1H) 7.49 (dd, J=8.84, 2.02 Hz, 1H) 7.54 - 7.65 (m, 1H) 7.94 (d, J=1 .77 Hz, 1H) 8.46 (d, J=2.78 Hz, 1H).b) 7-bromoquinolin-3-amineA suspension of 2-(7-bromoquinolin-3 -yl)isoindoline- 1, 3 -dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid wasdissolved in warm ethanol and adsorbed onto silica gel. Purification by silica gel chromatography (50-100percent ethyl acetate/hexanes) afforded the title compound (3.5 g, 5 6percent). ‘H NMR (400 MHz, DMSO-d6) 0 ppm 5.83 (s, 2 H) 7.14 (d, J=2.53 Hz, 1 H) 7.49 (dd, J8.84, 2.02 Hz, 1 H) 7.54 - 7.65 (m, 1 H) 7.94 (d, J1.77 Hz, 1 H) 8.46 (d, J=2.78 Hz, 1 H).A suspension of 2-(7-bromoquinolin-3-yl)isoindoline-l, 3-dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid was dissolved in warm ethanol and adsorbed onto silica gel. Purification by silica gel chromatography (50-100percent ethyl acetate/hexanes) afforded the title compound (3.5 g, 56percent>). 1H NMR (400 MHz, DMSO-dA suspension of 2-(7-bromoquinolin-3-yl)isoindoline-1 , 3-dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid was dissolved in warm ethanol and adsorbed onto silica gel. Purification of the solid by silica gel chromatography (50-100percent ethyl acetate/hexanes) afforded the title compound (3.5 g, 56percent).

Molecular Weight:223.07
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:221.97926
Monoisotopic Mass:221.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes