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

HRID 487389ノート

反応式

HRID 487389 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=[O:13].C([C:16](CC)([C:20]([O-:22])=O)[C:17]([O-:19])=[O:18])C.[CH2:25](O)[CH3:26]>N1CCCCC1>[CH2:10]([C:4]1[N:5]=[C:6]([CH2:8][CH3:9])[CH:7]=[C:2]2[C:3]=1[C:12]([OH:13])=[C:16]([C:17]([O:19][CH2:25][CH3:26])=[O:18])[C:20](=[O:22])[NH:1]2)[CH3:11]

参加物

5

反応物 3

HCID 702EthanolHCID 69515632,2-DiethylpropanedioateHCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 1

HCID 8082Piperidine触媒

実験手順

4-amino-2,6-diethylpyridine-3-carbaldehyde (1.78 g), diethylmalonate (1.92 g), ethanol (15 ml) and piperidine (4 drops) were heated at reflux for 16 hours. Volatile material was removed by evaporation and the residue was recrystallised from ethyl acetate/petroleum ether to give ethyl 5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate (B) (1.4 g), m.p. 159°-160° C.; NMR (CDCl3): 1.34(t, 3H), 1.38(t, 3H), 1.47(t, 3H), 2.87(q, 2H), 3.14(q, 2H), 4.47(q, 2H), 7.03(s, 1H), 8.78(s, 1H), 12.2(s, 1H); mass spectrum (CI, ammonia): 275 (M+H)+ ; microanalysis, found: C, 65.8; H, 6.8; N, 10.4%; C15H18N2O3 requires: C, 65.7; H, 6.6; N, 10.2%.

後処理

  1. temperatureat reflux for 16 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was recrystallised from ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-9c17c46f14f949cd908330fb5aa817d4
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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