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

HRID 53760ノート

反応式

HRID 53760 の反応式
[I:1][C:2]1[CH:11]=[C:10]([Cl: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.[OH-].[K+]>[I:1][C:2]1[C:11]([N+:15]([O-:17])=[O:16])=[C:10]([Cl: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

5

反応物 2

HCID 24434Potassium NitrateHCID 199585625-Iodo-7-chloro-1,4-dihydro-2,3-quinoxalinedione

生成物 1

HCID 199586055-Iodo-6-nitro-7-chloro-1,4-dihydro-2,3-quinoxalinedione収率 67%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 14797Potassium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

The method of Cheeseman, G. W. H. (J. Chem. Soc. 1170 (1962)) was adapted. 5-Iodo-7-chloro-1,4-dihydro-2,3-quinoxalinedione (96 mg, 0.33 mMol) was dissolved in concentrated H2SO4 (1.0 mL) at 0° C. for 30 min and then KNO3 (36 mg, 0.36 mMol, Baker) was added into this solution. The mixture was stirred at 0° C. for 0.5 h and then at room temperature for 30 h. It was poured into ice water (5 g). A precipitate came out and was collected by filtration giving 101 mg of crude title compound. The sample was dissolved in 1N KOH (5 mL) and then red precipitate was removed by filtration. The filtrate was acidified to pH=2 with 4N HCl to give a brown precipitate which was collected by filtration and then dried in air at 50° C. for 4 h. The title compound (75 mg, 67%) was obtained as a brown powder. Crystallization from DMSO/H2O afforded pure compound (34 mg) as brown microcrystals, mp: 388°-90° C. IR (KBr, cm-1): 3462, 3200, 3050, 1712, 1587, 1537. NMR (1H, DMSO-d6): δ 7.289 (s, 1H), 10.846 (s, 1H), 12.225 (s, 1H). HRMS: calcd for C8H3N3O4ClI (M+) m/z: 366.8855, found pending. Potency relative to DCK: partially active.

後処理

  1. waitat room temperature for 30 h
  2. filtrationwas collected by filtration
  3. customgiving 101 mg of crude title compound
  4. customred precipitate was removed by filtration
  5. customto give a brown precipitate which
  6. filtrationwas collected by filtration
  7. customdried in air at 50° C. for 4 h

出典と根拠

ORDレコード
ord-be49f4fac9824cb397f1607b4319efe4
出典データセット
uspto-grants-1997_04
特許番号
US05620979

反応ノート

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