Phosphorus oxychloride → HCID 59699571, 화합물

HRID 901229노트

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HRID 901229 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

HCID 59699571HCID 59699571, 화합물수율 98%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf831a6597154d6cbd9043a8398a68d6
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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