Hydrochloric Acid → 6-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione

HRID 1488967

반응식

HRID 1488967 반응식
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].[OH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[OH-].[K+].Cl>CS(C)=O>[N+:14]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:21]1[CH:22]=[CH:23][C:18](=[O:17])[CH:19]=[CH:20]1)[NH:9][C:8](=[O:12])[C:7](=[O:13])[NH:6]2)([O-:16])=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 99912306-Fluoro-7-nitro-1,4-dihydroquinoxaline-2,3-dioneHCID 178418642HCID 178418642, 화합물

생성물 1

HCID 98611296-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione수율 62.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

First, 9.007 g of 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione, 7.611 g of 4-hydroxypyridine, and 5.219 g of powdered potassium hydroxide were added to 120 ml of dry dimethylsulfoxide. The mixture was stirred at 130° C. for 2 hours in a nitrogen atmosphere. Then, 50 ml of ice water and 30 ml of 4N hydrochloric acid were added to the reaction mixture so as to make it weakly acidic (pH 3 to 4). The resultant yellow precipitate was filtered and washed with water. The precipitate was dissolved by heating in a mixture containing 560 ml of water and 56 ml of conc. aqueous ammonia. One gram of activated carbon was added to the resultant mixture, stirred, and filtered. The filtrate was neutralized with conc. hydrochloric acid and ice-cooled. The precipitated crystals were then filtered and washed with water, methanol, and ethanol, successively. The resultant crystals were dried to give 7.56 g of 6-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione (hereinafter, abbreviated as Ia).

후처리

  1. filtrationThe resultant yellow precipitate was filtered
  2. washwashed with water
  3. dissolutionThe precipitate was dissolved
  4. temperatureby heating in a mixture
  5. additioncontaining 560 ml of water and 56 ml of conc. aqueous ammonia
  6. additionOne gram of activated carbon was added to the resultant mixture
  7. stirringstirred
  8. filtrationfiltered
  9. temperaturecooled
  10. filtrationThe precipitated crystals were then filtered
  11. washwashed with water, methanol, and ethanol
  12. customThe resultant crystals were dried

출처 및 근거

ORD 기록
ord-08ff0463da474729a90d3320dd332b50
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677305

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