Diethyl Oxalate → 1,4-Dihydrobenzo[g]quinoxaline-2,3-dione

HRID 984844

반응식

HRID 984844 반응식
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:13](OCC)(=[O:19])[C:14](OCC)=[O:15]>>[NH:1]1[C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]3=[CH:10][C:11]=2[NH:12][C:14](=[O:15])[C:13]1=[O:19]

참가 물질

3

반응물 2

HCID 7268Diethyl OxalateHCID 698722,3-Diaminonaphthalene

생성물 1

HCID 108224091,4-Dihydrobenzo[g]quinoxaline-2,3-dione수율 82%

실험 절차

A mixture of 2,3-diaminonaphthalene (2.87 g, 18.14 mmol) and diethyl oxalate (30 mL, 223 mmol) was heated to reflux for 14 hours, cooled to RT and filtered. The residue was washed with EtOH and dried in vacuo to give the title compound as a brown solid (3.15 g, 82%); mp>350° C.; IR (KBr, cm−1) 3045, 2942, 2869,1716, 1642,1406, 877; 1H NMR (DMSO) δ 12.11 (s, 2H), 7.84-7.81 (m, 2H), 7.54 (s, 2H) 7.39 (dd, J=6.3, 3.0, 2H); LC/MS 92.5% (220 nm), m/z (M+H+) 213.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 14 hours
  3. filtrationfiltered
  4. washThe residue was washed with EtOH
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-9f035cb72da04937aeb215663ac9e01c
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869956B2

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