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

HRID 984844

反応式

HRID 984844 の反応式
[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]

参加物

3

反応物 2

HCID 7268Diethyl OxalateHCID 698722,3-Diaminonaphthalene

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9f035cb72da04937aeb215663ac9e01c
出典データセット
uspto-grants-2005_03
特許番号
US06869956B2

関連ノート

読み込み中…