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

HRID 53745ノート

反応式

HRID 53745 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

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): δ 7.146 (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.

後処理

  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

出典と根拠

ORDレコード
ord-0beecf167572474eb487113e086f6717
出典データセット
uspto-grants-1997_04
特許番号
US05620979

反応ノート

読み込み中…