Diethyl Ether → Ethyl 4-hydroxy-1,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 2058180ノート

反応式

HRID 2058180 の反応式
[CH3:1][NH:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].C([CH:16]([C:20](Cl)=[O:21])[C:17](Cl)=[O:18])C.[CH2:23]([O:25]CC)[CH3:24]>>[CH2:23]([O:25][C:20]([C:16]1[C:17](=[O:18])[N:2]([CH3:1])[C:3]2[C:4]([C:5]=1[OH:6])=[CH:9][CH:10]=[C:11]([CH3:13])[N:12]=2)=[O:21])[CH3:24]

参加物

4

反応物 3

HCID 3283Diethyl EtherHCID 109209242-Ethylpropanedioyl dichlorideHCID 13952725HCID 13952725、化合物

生成物 1

HCID 54696181Ethyl 4-hydroxy-1,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

実験手順

To a solution of 9.0 g. (0.05 mole) of methyl 2-methylamino-6-methylnicotinate in 150 ml. of anhydrous diethyl ether was added 3.75 g. (0.025 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was dissolved in 10 ml. of ethanol. This solution was added to a solution of 1.15 g. (0.05 g. atoms) of sodium in 75 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes and was filtered. The filter cake was triturated with 100 ml. of water and this mixture was acidified with glacial acetic acid. The insoluble material was collected, air dried and was recrystallized from ethyl acetate to give 1.5 g. of the title compound, m.p. 143°-5° C.

後処理

  1. filtrationThe mixture was filtered
  2. dissolutionthe filtrate was dissolved in 10 ml
  3. additionThis solution was added to a solution of 1.15 g
  4. stirringThe mixture was stirred at room temperature for 5 minutes
  5. filtrationwas filtered
  6. customThe filter cake was triturated with 100 ml
  7. customThe insoluble material was collected
  8. customair dried
  9. customwas recrystallized from ethyl acetate
  10. customto give 1.5 g

出典と根拠

ORDレコード
ord-b4964783806544f3b9b12188f72654c5
出典データセット
uspto-grants-1980_07
特許番号
US04215123

反応ノート

読み込み中…