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

HRID 513120ノート

反応式

HRID 513120 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-747bccec854845cba2c0ea81bada9717
出典データセット
uspto-grants-2015_08
特許番号
US09102678B2

反応ノート

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