Phosphorus oxychloride → HCID 59699571、化合物

HRID 901229ノート

反応式

HRID 901229 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:27]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1[Cl:27])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 54729304Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

生成物 1

HCID 59699571HCID 59699571、化合物収率 98%

実験手順

A solution of 1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (3) (0.94 g, 2.9 mmol) was heated in neat POCl3 at 90° C. for 3 h. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in water, neutralized by solid NaHCO3, and extracted by dichloromethane. The organic layer was subsequently washed by saturated NaHCO3 solution, water and brine, dried over Na2SO4, and evaporated to yield 0.9 g (98%) of 1-benzyl-4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (4) as white solids. MP: 109° C.; 1H-NMR (DMSO-d6): δ 1.31 (t, J=6.9 Hz, 3H), 4.37 (q, J=6.9 Hz, 2H), 5.62 (s, 2H), 7.27 (m, 5H), 7.51 (dd, J=4.7, 8.0 Hz, 1H), 8.46 (dd, J=1.5, 7.5 Hz, 1H), 8.80 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 343 (M+1), 365 (M+23).

後処理

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. extractionextracted by dichloromethane
  4. washThe organic layer was subsequently washed by saturated NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-bf831a6597154d6cbd9043a8398a68d6
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

反応ノート

読み込み中…