7-broMoquinolin-3-aMine synthesis
- Product Name:7-broMoquinolin-3-aMine
- CAS Number:1266322-58-0
- Molecular formula:C9H7BrN2
- Molecular Weight:223.07
1375108-38-5
1266322-58-0
b) Synthesis of 7-bromoquinolin-3-amine: 2-(7-bromoquinolin-3-yl)isoindoline-1,3-dione (10 g, 28.3 mmol) was suspended in ethanol (200 mL), hydrazine (1.777 mL, 56.6 mmol) was added, followed by heating and refluxing for 1 hour. After completion of the reaction, the mixture was allowed to cool to room temperature and the precipitate was collected and washed with a small amount of ethanol. The filtrate was concentrated to dryness to give a gray solid. The resulting solid was dissolved in warm ethanol and adsorbed on silica gel. Purification by silica gel column chromatography (eluent: 50-100% ethyl acetate/hexane gradient) afforded the target compound 7-bromoquinolin-3-amine (3.5 g, 56% yield).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, 2.02Hz, 1H), 7.54-7.65 (m, 1H), 7.94 (d, J = 1.77Hz, 1H), 8.46 (d, J = 2.78Hz, 1H).
1375108-38-5
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1266322-58-0
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Yield: 97%
Reaction Conditions:
with hydrazine hydrate in ethanol for 1 h;Reflux;
Steps:
A.A87.3 Preparation of intermediate 397
A suspension of intermediate 396 ( 14 g, 38.5 mmol) in ethanol ( 1 50 mL) was treated with NH2 H2.H2O (4.5 g, 76.9 mmol ) and was re fluxed for l hour. The mixture was al lowed to cool and filtered. The filtrate was col lected and evaporated to obtain intermediate 397 (8.6 g, 94% yield).
References:
JANSSEN PHARMACEUTICA NV;WU, Tongfei;BREHMER, Dirk;BEKE, Lijs;BOECKX, An;DIELS, Gaston, Stanislas, Marcella;GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph;LAWSON, Edward, Charles;PANDE, Vineet;PARADE, Marcus, Cornelis, Bernardus, Catharina;SCHEPENS, Wim, Bert, Griet;THURING, Johannes, Wilhelmus, John, F;VIELLEVOYE, Marcel;SUN, Weimei;MEERPOEL, Lieven WO2017/32840, 2017, A1 Location in patent:Page/Page column 265; 266
59278-65-8
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135484-83-2
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1266322-58-0
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946122-05-0
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1266322-58-0
40 suppliers
$52.00/100mg