Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate → 5,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-one

HRID 487383ノート

反応式

HRID 487383 の反応式
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[C:6](C(OCC)=O)[C:7](=[O:15])[NH:8]2)[CH3:2]>O.O1CCOCC1.Cl>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[CH:6][C:7](=[O:15])[NH:8]2)[CH3:2]

参加物

5

反応物 1

HCID 54684680Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

生成物 1

HCID 546846815,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-one収率 55.9%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Compound B (1 g) was dissolved in a mixture of water (1 ml), 1,4-dioxan (2 ml) and concentrated hydrochloric acid (1 ml) and the mixture was heated at reflux for 3 hours. The reaction mixture was then cooled and the suspended solid was collected by filtration. The solid was washed with ethanol and ether and dried under vacuum to give 5,7-diethyl-4-hydroxy-1,6-naphthyridin-2(1H)-one (C) (0.42 g), m.p. 322°-325° C.; NMR (d6 -DMSO): 1.3(dt, 6H), 2.99(q, 2H), 3.47(q, 2H), 6.0(s, 1H), 7.28(s, 1H), 12.3(s, 1H); mass spectrum (CI, ammonia): 219 (M+H)+ ; microanalysis, found: C, 55.7; H, 5.9; N, 10.5%; C12H14N2O2.HCl.0.25H2O requires: C, 55.6; H, 5.6; N, 10.8%.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationthe suspended solid was collected by filtration
  5. washThe solid was washed with ethanol and ether
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-32ec258398e244f89cb828ac326830b0
出典データセット
uspto-grants-1994_03
特許番号
US05294620

反応ノート

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