Triethylamine → 4,6-Dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

HRID 901256노트

반응식

HRID 901256 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]2[C:14]([C:15]=1O)=[CH:13][C:12]([Cl:17])=[CH:11][N:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:37]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]2[C:14]([C:15]=1[Cl:37])=[CH:13][C:12]([Cl:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 547385986-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

생성물 1

HCID 692156984,6-Dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester수율 85%

실험 절차

A solution of 6-chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (75) (6.0 g, 15.43 mmol) and triethylamine (5.36 mL, 38.57 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 saturated NaHCO3 solution, sonicated briefly and filtered. The solids were dissolved in dichloromethane, washed subsequently by saturated NaHCO3 solution, water and brine. The organic phase was dried over MgSO4 and evaporated to yield 6.2 g (85%) of 4,6-dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (77) as yellow waxy solids. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.2 Hz, 3H), 3.69 (s, 3H), 4.38 (q, J=7.2 Hz, 2H), 5.50 (s, 2H), 6.82 (m, 2H), 7.24 (m, 2H), 8.48 (d, J=2.4 Hz, 1H), 8.87 (d, J=2.4 Hz, 1H); EIMS: 407 (M).

후처리

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. dissolutionThe solids were dissolved in dichloromethane
  6. washwashed subsequently by saturated NaHCO3 solution, water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-df795b11e3054887aafd25da1d08304f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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