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

HRID 54406ノート

反応式

HRID 54406 の反応式
[Br:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]=[N:5]2.[N+]([O-])([O-])=[O:18].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[O:18])[NH:5]2

参加物

4

反応物 2

HCID 24434Potassium NitrateHCID 211899856-Bromo-7-chloro-5-nitroquinoxaline-2(1H)-one

生成物 1

HCID 104037516-Bromo-7-chloro-5-nitro-1,4-dihydro-2,3-quinoxalinedione収率 50%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

To a stirred solution of 6-bromo-7-chloro-5-nitroquinoxaline-2(1H)-one (0.025 g, 0.082 mmol) in conc. H2SO4 (0.5 mL) was added KNO3 (0.011 g, 0.11 mmol) and the resulting dark red solution was stirred at r.t. for 65 h. The solution was then cooled in an ice-bath and diluted with ice to a total volume of 5.0 mL. The precipitated solid was filtered, washed with water (2.0 mL) and dried under vacuum to give 0.019 g (72%) of crude product. It was purified as follows. Crude product (0.016 g) was taken up in 1N NaOH (1.1 mL). The mixture was centrifuged and the supernatant liquid was acidified with conc. HCl to pH~2. The precipitated solid was filtered, washed with water (1.0 mL) and dried under vacuum to furnish 0.010 g (50%) of pure title compound as a cream colored powder; m.p. 338°-343° C. (decomposed); 1H NMR (DMSO-d6): 7.35 1 (s, 1H), 12.25 1 (s overlapped by a br s, 2H).

後処理

  1. temperatureThe solution was then cooled in an ice-bath
  2. additiondiluted with ice to a total volume of 5.0 mL
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (2.0 mL)
  5. customdried under vacuum
  6. customto give 0.019 g (72%) of crude product
  7. customIt was purified
  8. filtrationThe precipitated solid was filtered
  9. washwashed with water (1.0 mL)
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-74d407f01a4b4db4ab2e20a303453c75
出典データセット
uspto-grants-1997_04
特許番号
US05622952

反応ノート

読み込み中…