7-FLUORO-6-METHOXYISOQUINOLIN-1(2H)-ONE synthesis
- Product Name:7-FLUORO-6-METHOXYISOQUINOLIN-1(2H)-ONE
- CAS Number:630422-98-9
- Molecular formula:C10H8FNO2
- Molecular Weight:193.17
1409964-67-5
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630422-98-9
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Yield:630422-98-9 67%
Reaction Conditions:
Stage #1: (E)-3-(4-fluoro-3-methoxyphenyl) acryloyl azide in 1,2-dichloro-benzene at 140; for 1 h;
Stage #2: iodine in 1,2-dichloro-benzene at 180; for 1.5 h;
Steps:
3
A solution of the acyl azide (39 g, see Example 2) in 1,2-dichlorobenzene (300 mL) was heated to 140°C for approximately Ih until gas formation subsides. Catalytic iodine was added and the temperature was increased to 180°C for 1. 5h. The reaction mixture was allowed to cool to ambient temperature with stirring; the precipitate which formed was collected by filtration, washed with benzene and dried under vacuum to afford 22.6 g (67%) of 7-fluoro-6-methoxy-2H-isoquinolin-1-one as a tan solid. RP-HPLC: 2.58 min; ES-MS (M+H) += 194.1 ; 1H-NMR (DMSO-d6) 8 (ppm): 3.8 (3H, s), 6.48 (l, d), 7.11 (t, 1), 7.33 (d, 1) ; 6.77 (d, 1).
References:
WO2005/35520,2005,A1 Location in patent:Page/Page column 23
630424-79-2
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630422-98-9
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128495-46-5
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630422-98-9
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$45.00/10mg