Diethyl Oxalate → 1-Methyl-1,4-dihydro-2,3-quinoxalinedione

HRID 53733

反応式

HRID 53733 の反応式
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19]>>[CH3:11][N:12]1[C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:19][C:1](=[O:8])[C:2]1=[O:4]

参加物

3

反応物 2

HCID 7268Diethyl OxalateHCID 78498N-Methyl-o-phenylenediamine

生成物 1

HCID 6006271-Methyl-1,4-dihydro-2,3-quinoxalinedione

実験手順

N-Methyl-1,4-dihydro-2,3-quinoxalinedione was prepared using an adaptation of the method of Cheeseman (J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (3.23 g, 22.1 mmol) and N-methyl-1,2-diaminobenzene (332 mg, 2.72 mmol) was heated to reflux under N2 for 2 h. The reaction was allowed to cool to room temperature and the solid collected by vacuum filtration and rinsed with EtOH. The gray brown solid was further dried under vacuum (0.1 torr, 25° C.) to give 274.3 mg (57.2%). A portion of this solid was further purified by recrystallization from 50 mL EtOH and treatment with activated charcoal to give fluffy pale yellow crystals which were collected by vacuum filtration and rinsed with cold EtOH to yield 104.9 mg. 1H NMR (d6 -DMSO) δ 3.50 (s, 3H, CH3), 7.16 (m, 3H, ArH), 7.36 (m, 1H, ArH), 12.01 (s, 1H, NH). EIMS 176 (M+, 52), 148 (33), 119 (100, bp).

後処理

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 2 h
  3. filtrationthe solid collected by vacuum filtration
  4. washrinsed with EtOH
  5. customThe gray brown solid was further dried under vacuum (0.1 torr, 25° C.)
  6. customto give 274.3 mg (57.2%)
  7. customA portion of this solid was further purified by recrystallization from 50 mL EtOH and treatment with activated charcoal
  8. customto give fluffy pale yellow crystals which
  9. filtrationwere collected by vacuum filtration
  10. washrinsed with cold EtOH
  11. customto yield 104.9 mg

出典と根拠

ORDレコード
ord-31050766590f4082bea79fb99f358d48
出典データセット
uspto-grants-1997_04
特許番号
US05620979

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