Hydrochloric Acid → HCID 22903574, compound

HRID 1488980Notes

Reaction equation

F[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[OH:24].[OH-].[K+].Cl>CS(C)=O>[N+:14]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:20]1[CH:21]=[CH:22][C:23](=[O:24])[C:18]([F:17])=[CH:19]1)[NH:9][C:8](=[O:12])[C:7](=[O:13])[NH:6]2)([O-:16])=[O:15]

Participants

Conditions

Temperature: 130 °C

Procedure

First, 127 mg of 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione, 96 mg of 3-fluoro-4-hydroxypyridine, and 55 mg of powdered potassium hydroxide were added to 12 ml of dry dimethylsulfoxide. The mixture was stirred at 130° C. for 3 hours in a nitrogen atmosphere. Then, 50 ml of ice water was added to the reaction mixture, and the mixture was neutralized with 2N hydrochloric acid. The resultant precipitate was filtered and washed with water. The precipitate was dissolved in 3 ml of 1N sodium hydroxide. The solution was treated with activated carbon and filtered. The filtrate was neutralized with conc. hydrochloric acid. The precipitated crystals were filtered and dried to give 147 mg of 6-nitro-7-(3-fluoro-4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione.

Workup

filtrationThe resultant precipitate was filtered
washwashed with water
dissolutionThe precipitate was dissolved in 3 ml of 1N sodium hydroxide
additionThe solution was treated with activated carbon
filtrationfiltered
filtrationThe precipitated crystals were filtered
customdried

Sources & evidence

ORD record: ord-791c9cb52d2f45b2a3a29e2b68bda1d1
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677305

Reaction notes

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