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

HRID 462692ノート

反応式

HRID 462692 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f245ba153a44ed4b5a51543f16446cb
出典データセット
uspto-grants-1985_05
特許番号
US04517191

反応ノート

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