Potassium Carbonate → Ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 462692노트

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HRID 462692 반응식
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:24](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:24][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[N:11]=2)[C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 5373687Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

생성물 1

HCID 13457701Ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate수율 63.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 9.7 g (0.0417 m) of ethyl 1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate, 11.5 g (0.0834 m) of potassium carbonate and 200 ml of dimethylformamide was slurried at room temperature, and 8.3 g (0.0417 m) of O-(2,4-dinitrophenyl)hydroxylamine was added. The reaction mixture was stirred for 17 hours and then concentrated in vacuo. The residue was dissolved in 1 liter of warm water and extracted with 800 ml of chloroform. The extracts were filtered, dried over anhydrous magnesium sulfate, decolorized with charcoal and concentrated in vacuo. The residue was recrystallized from ethanol and chromatographed on silica gel, using isopropyl alcohol-chloroform (1:9) for elution, to give 6.5 g of ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate, buff-colored solid, m.p. 173°-174° C. when recrystallized from ethanol.

후처리

  1. customwas slurried at room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 1 liter of warm water
  4. extractionextracted with 800 ml of chloroform
  5. filtrationThe extracts were filtered
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethanol
  9. customchromatographed on silica gel
  10. washfor elution

출처 및 근거

ORD 기록
ord-1f245ba153a44ed4b5a51543f16446cb
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04517191

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