Potassium Nitrate → 5-Bromo-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedione

HRID 439465노트

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HRID 439465 반응식
[Br:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2.[N+:15]([O-])([O-:17])=[O:16].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[C:11]([N+:15]([O-:17])=[O:16])=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2

참가 물질

4

반응물 2

HCID 24434Potassium NitrateHCID 211900395-Bromo-7-fluoro-1,4-dihydroquinoxaline-2,3-dione

생성물 1

HCID 199586215-Bromo-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedione수율 90%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
0 °C

실험 절차

The method of Cheeseman, supra. was adapted. 5-Bromo-7-fluoro-1,4-dihydroquinoxaline-2,3-dione (77 mg, 0.30 mMol) was dissolved in concentrated H2SO4 (1 mL) at 0° C. for 30 min, and KNO3 (35 mg, 0.346 mMol, Baker) was added to this solution. The mixture was stirred at 0° C. for 3 h and then at room temperature for 30 h. The mixture was poured into ice water (10 g) and the precipitate was collected by filtration. The precipitate was dissolved in 1N NaOH (10 mL), then was acidified to pH=2 with 4N HCl to give cream precipitate, which was collected by filtration, and was dried in the air at 50° C. for 4 h affording pure (by NMR) 5-bromo-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedione (81 mg, 90%), as a white amorphous solid; mp: 320°-25° C. (dec. from 290° C.). IR (KBr, cm-1): 3416, 3071, 2952, 1721, 1609, 1546. NMR (1H, DMSO-d6): δ7.146 (d, J=10.2 Hz, 1H), 11.432 (s, 1H), 12.340 (s, 1H). HRMS: calcd. for C8H3N3O4BrF (M+) m/z: 302.9290, found: 302.9290.

후처리

  1. waitat room temperature for 30 h
  2. filtrationthe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in 1N NaOH (10 mL)
  4. customto give cream precipitate, which
  5. filtrationwas collected by filtration
  6. customwas dried in the air at 50° C. for 4 h

출처 및 근거

ORD 기록
ord-31abc5c0b6764253905a2480b0af7808
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514680

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