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

HRID 54307

반응식

HRID 54307 반응식
[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]

참가 물질

4

반응물 2

HCID 7268Diethyl OxalateHCID 7372853,4-Diaminobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08d71a57b5484c339d8d469cb15cbcea
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622952

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