Phosphorus oxychloride → 2-Chloro-4-(4-fluorophenyl)-7-methylquinoline

HRID 2422549노트

반응식

HRID 2422549 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.C([O-])(O)=O.[Na+]>>[Cl:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[N:11]=1

참가 물질

4

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 574378424-(4-Fluorophenyl)-7-methylquinoline

생성물 1

HCID 866219782-Chloro-4-(4-fluorophenyl)-7-methylquinoline

실험 절차

A solution of 4-(4-fluorophenyl)-7-methylquinoline (3.09 g, 12.2 mmol) in phosphorus oxychloride (8 mL, 85.8 mmol) was stirred 30 min. at 90° C. The mixture was poured slowly into an aqueous saturated solution of NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29) gave the title compound. MS (+ESI): 271 (M+H)+.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29)

출처 및 근거

ORD 기록
ord-70b02feae16d4e10bec38f51d393c9a6
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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