Hydrochloric Acid → HCID 22903583, compound

HRID 1488975Notes

Reaction equation

F[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:16])[C:8](=[O:15])[N:9]2[CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[OH:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.[OH-].[K+].Cl>O.CS(C)=O>[N+:17]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:24]1[CH:25]=[CH:26][C:21](=[O:20])[CH:22]=[CH:23]1)[N:9]([CH2:12][CH2:13][CH3:14])[C:8](=[O:15])[C:7](=[O:16])[NH:6]2)([O-:19])=[O:18]

Participants

Conditions

Temperature: 130 °C

Procedure

First, 1.244 g of 7-fluoro-6-nitro-1-(n-propyl)-1,4-dihydroquinoxaline-2,3-dione, 952 mg of 4-hydroxypyridine, and 711 mg of powdered potassium hydroxide were added to 10 ml of dry dimethylsulfoxide. The mixture was stirred at 130° C. for 3.5 hours in a nitrogen atmosphere. Then, 50 ml of water was added to the reaction mixture and the mixture was made acidic (pH 2 to 3) with 4N hydrochloric acid to give a yellow precipitate. The precipitate was filtered and recrystallized with dimethylformaldehyde to give 1.08 g of 6-nitro-7-(4-oxo-4H-pyridin-1-yl)-1-(n-propyl)-1,4-dihydroquinoxaline-2,3-dione.

Workup

customto give a yellow precipitate
filtrationThe precipitate was filtered
customrecrystallized with dimethylformaldehyde

Sources & evidence

ORD record: ord-185274fda953490ea3573cbe66255554
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677305

Reaction notes

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