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

HRID 2058180노트

반응식

HRID 2058180 반응식
[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]

참가 물질

4

반응물 3

HCID 3283Diethyl EtherHCID 109209242-Ethylpropanedioyl dichlorideHCID 13952725HCID 13952725, 화합물

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4964783806544f3b9b12188f72654c5
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04215123

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