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

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

반응물 2

HCID 7268Diethyl Oxalate

HCID 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

temperaturewas heated
temperatureto reflux for 14 hours
filtrationfiltered
washThe residue was washed with EtOH
customdried in vacuo

출처 및 근거

ORD 기록: ord-9f035cb72da04937aeb215663ac9e01c
출처 데이터셋: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06869956B2

반응 노트

불러오는 중…