Sodium Hydroxide → 3-Hydroxy-5-methyl-1,6-naphthyridin-2(1H)-one

E-5. 3-Hydroxy-5-methyl-1,6-naphthyridin-2-(1H)-one--This compound was prepared by heating 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one following in part the procedure described in Example E-4 without purification of 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one by reacting said unpurified 3-amino compound with aqueous sodium hydroxide solution or by similarly reacting said purified 3-amino compound with aqueous sodium hydroxide solution. These procedures are described as follows. Following the procedure described in Example E-4 using 27 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carboxylic acid hydrazide, 60 ml of concentrated sulfuric acid, 200 ml of water and 9.1 g of sodium nitrite and after concentrating the reaction mixture to dryness on a rotary evaporator, the residue containing the corresponding said 3-amino compound was treated with 75 ml of 35% sodium hydroxide solution and 100 ml of water and the resulting aqueous mixture was heated on a steam bath for 30 hours and then acidified with acetic acid. The acidified mixture was allowed to stand at room temperature overnight and the resulting product that separated was collected, washed with water and air-dried. It was then recrystallized from 400 ml of boiling dimethylformamide, filtering off the insoluble material, concentrating the filtrate to a volume of about 200 ml and then allowing it to stand at room temperature for 3 hours. The yellow crystalline solid was collected, washed with methanol and dried at 100° C. to yield 7.6 g of 3-hydroxy-5-methyl-1,6-naphthyridin-2-(1H)-one, m.p.>320° C. The same compound was also prepared by heating a mixture containing 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one with 25 ml of 10% aqueous sodium hydroxide solution on a steam bath for 7 hours and then cooled to room temperature The reaction mixture was acidified with acetic acid and the resulting white crystalline precipitate was collected, washed with water and dried at 95° C. to yield 1.2 g of 3-hydroxy-5-methyl-1,6-naphthyridin-2(1H)-one, m.p.>320° C.

1. customby similarly reacting said purified 3-amino compound with aqueous sodium hydroxide solution
2. concentrationafter concentrating the reaction mixture to dryness
3. customon a rotary evaporator
4. additionthe residue containing the
5. additionwas treated with 75 ml of 35% sodium hydroxide solution and 100 ml of water
6. temperaturethe resulting aqueous mixture was heated on a steam bath for 30 hours
7. customthe resulting product that separated
8. customwas collected
9. washwashed with water
10. customair-dried
11. customIt was then recrystallized from 400 ml of boiling dimethylformamide
12. filtrationfiltering off the insoluble material
13. concentrationconcentrating the filtrate to a volume of about 200 ml
14. waitto stand at room temperature for 3 hours
15. customThe yellow crystalline solid was collected
16. washwashed with methanol
17. customdried at 100° C.

ORD record

ord-3ddb63c222884c4b9bf4d9062392f2e3

Source dataset

uspto-grants-1985_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04517190