ChemicalBook CAS DataBase List 1,5-dihydro-1,5-Naphthyridine-2,6-dione

1,5-dihydro-1,5-Naphthyridine-2,6-dione synthesis

7synthesis methods

Product Name:1,5-dihydro-1,5-Naphthyridine-2,6-dione
CAS Number:27017-70-5
Molecular formula:C8H6N2O2
Molecular Weight:162.15

27017-64-7 Synthesis

27017-64-7
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27017-70-5
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Yield:27017-70-5 87%

Reaction Conditions:

with hydrogen bromide in water;

Steps:

7 1,5-Dihydro-[1,5]naphthyridine-2,6-dione

1,5-Dihydro-[1,5]naphthyridine-2,6-dione
To a solution of 48% HBr in water (45 cm³) is added 6-methoxy-1H-[1,5]naphthyridin-2-one (1.90 g, 10.8 mmol) and the reaction mixture is heated to reflux for 2.5 hours.
The reaction mixture is then cooled to 22° C. and adjusted to pH 7 with aqueous sodium carbonate, the resulting suspension is then cooled to 0° C. and the solids collected by filtration to yield the product as a beige solid (1.53 g, 87%).
¹H NMR (300 MHz, TFA-d) 7.47 (1H, d, ArH, J=9.8), 7.33 (1H, d, ArH, J=9.0), 6.71 (1H, d, ArH, J=8.9), 6.35 (1H, d, ArH, J=9.7), 3.55 (3H, s, CH₃).

References:

US2015/144846,2015,A1 Location in patent:Page/Page column