Sodium Hydroxide → (2-Amino-5-chlorophenyl)(4-methoxyphenyl)methanone

HRID 2100393노트

반응식

HRID 2100393 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C2C=CC(F)=CC=2)=[C:4]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=2)[CH:3]=1.NC1C=CC(Cl)=CC=1[C:35](C1C=CC=C(OC)C=1)=[O:36].[OH-].[Na+]>CO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:18]([C:19]1[CH:20]=[CH:21][C:22]([O:36][CH3:35])=[CH:23][CH:24]=1)=[O:26]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 12325894(2-Amino-5-chlorophenyl)(3-methoxyphenyl)methanoneHCID 67505636N-[4-chloro-2-(4-fluoro-benzoyl)-phenyl]-4-fluoro-benzamide

생성물 1

HCID 347770(2-Amino-5-chlorophenyl)(4-methoxyphenyl)methanone수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of N-[4-chloro-2-(4-fluoro-benzoyl)-phenyl]-4-fluoro-benzamide (6.0 g, 16 mmol), prepared as described above for compound 1s, in MeOH (400 mL) was added 5N NaOH (50 mL) and the resulting solution was allowed to reflux for 16 h. The solution was cooled to room temperature and concentrated in vacuo. The aqueous portion was extracted with CH2Cl2 (2×100 mL). The combined organic portions were washed with H2O (3×50 mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by column chromatography (silica gel, 5 to 25% EtOAc/hexanes) and recrystallized from MeOH to provide 1u (3.5 g, 83%) as a light yellow powder MS m/z=262 (M+H).

후처리

  1. temperatureto reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. extractionThe aqueous portion was extracted with CH2Cl2 (2×100 mL)
  4. washThe combined organic portions were washed with H2O (3×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting residue was purified by column chromatography (silica gel, 5 to 25% EtOAc/hexanes)
  9. customrecrystallized from MeOH

출처 및 근거

ORD 기록
ord-cf308dce9ae149549b196ed1f8ba7d86
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572784B2

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