Diethyl Oxalate → 2,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile

HRID 54307

反応式

HRID 54307 の反応式
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[NH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[NH2:20])[C:15]#[N:16]>C(O)(=O)C>[C:15]([C:14]1[CH:13]=[C:12]2[C:19](=[CH:18][CH:17]=1)[NH:20][C:1](=[O:8])[C:2](=[O:4])[NH:11]2)#[N:16]

参加物

4

反応物 2

HCID 7268Diethyl OxalateHCID 7372853,4-Diaminobenzonitrile

生成物 1

HCID 51006912,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

The title compound was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (3.90 g, 27.6 mmol) and 3,4-diaminobenzonitrile (275 mg, 2.06 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 yellow brown solid was air dried to yield 156.6 mg (40.8%) which was >98% pure by 1H NMR. An analytically pure sample was prepared by recrystallization of 100 mg in 10 mL glacial acetic acid to give 21.2 mg of fine white crystals. 1H NMR (d6 -DMSO) δ7.20 (d, J=8.1, 1H, ArH), 7.39 (d, J=1.2, 1H, ArH), 7.50 (dd, J=1.2, J=8.4, 1H, ArH), 12.09 (s, 1H, NH), 12.22 (s, 1H, NH). EIMS m/z 187(87, M+), 159 (100, bp), 131(83), 104 (77), 77 (65), 53 (43), 28 (30). EIHRMS calc. for C9H5N3O2 187.0381, found 187.0377.

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. customdried
  6. customto yield 156.6 mg (40.8%) which

出典と根拠

ORDレコード
ord-08d71a57b5484c339d8d469cb15cbcea
出典データセット
uspto-grants-1997_04
特許番号
US05622952

関連ノート

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