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

HRID 1587502ノート

反応式

HRID 1587502 の反応式
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[NH2:12][C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[N:16]=[C:15]([CH2:21][CH3:22])[C:14]=1[C:23](OC)=[O:24].[Na]>C(O)C>[CH2:21]([C:15]1[N:16]=[C:17]([CH2:19][CH3:20])[CH:18]=[C:13]2[C:14]=1[C:23]([OH:24])=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:3](=[O:5])[NH:12]2)[CH3:22]

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 20094263Methyl 4-amino-2,6-diethylpyridine-3-carboxylate

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 702Ethanol溶媒

反応条件

温度
150 °C

実験手順

Diethyl malonate (14.5 ml) and methyl 4-amino-2,6-diethylpyridine-3-carboxylate (21.3 g) was added to a solution of sodium (2.33 g) in ethanol (60 ml) and the resulting mixture was heated at 150° C. for 20 hours in an autoclave. The mixture was allowed to cool and then volatile material was removed by evaporation and the resultant semi-crystalline solid was triturated with ether. The solid was collected by filtration and dissolved in a minimum of water. The solution as acidified with 2M hydrochloric acid and the resulting precipitate was collected by filtration and washed with water. The solid was dried under vacuum to give ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate (B) (12.72 g); m.p. 240-242° C.; NMR (CDCl3): 1.34(dt, 6H), 1.52(t, 3H), 2.84(q, 2H), 3.36(q, 2H), 4.52(q, 2H), 6.87(s, 1H), 7.26(s, 1H), 11.41(broad, 1H); mass spectrum (CI, ammonia): 291 (M+H)+ ; microanalysis, found: C, 62.1; H, 6.2; N, 9.7%; C15H18N2O4 requires: C, 62.1; H, 6.3; N, 9.7%.

後処理

  1. temperatureto cool
  2. customvolatile material was removed by evaporation
  3. customthe resultant semi-crystalline solid was triturated with ether
  4. filtrationThe solid was collected by filtration
  5. dissolutiondissolved in a minimum of water
  6. filtrationthe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customThe solid was dried under vacuum

出典と根拠

ORDレコード
ord-ce9f4a271a794a70a5fa482dad255021
出典データセット
uspto-grants-1993_06
特許番号
US05217976

反応ノート

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