Ammonium Hydroxide → 8-Fluoro-6-methylphenanthridine

HRID 2224630ノート

反応式

HRID 2224630 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=O)[CH3:16])=[CH:4][CH:3]=1.[OH-].[NH4+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[C:15]([CH3:16])[N:14]=[C:9]3[C:8]=2[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:3]=1

参加物

3

反応物 2

HCID 14923Ammonium HydroxideHCID 16679975HCID 16679975、化合物

生成物 1

HCID 224823738-Fluoro-6-methylphenanthridine収率 94%

反応条件

温度
120 °C

実験手順

N-(4′-Fluorobiphenyl-2-yl)-acetamide (18.5 g, 80.7 mmol) was mixed with polyphosphoric acid (250 g) and then heated to 120° C. with vigorous stirring for 48 hours. The hot reaction mixture was poured onto ice and stirred vigorously until homogeneous. Concentrated ammonium hydroxide was added until the pH >9. A white precipitate formed. The mixture was filtered and the white solid was dissolved in ethyl acetate (250 mL) and filtered. The filtrate was washed with saturated, aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and reduced in vacuo to a brown solid. The solid was purified by recrystallization from ethyl acetate-hexane to afford 8-fluoro-6-methylphenanthridine as white crystals (15.9 g, 94% ), m.p. 92-93° C.

後処理

  1. additionThe hot reaction mixture was poured onto ice
  2. stirringstirred vigorously until homogeneous
  3. customA white precipitate formed
  4. filtrationThe mixture was filtered
  5. dissolutionthe white solid was dissolved in ethyl acetate (250 mL)
  6. filtrationfiltered
  7. washThe filtrate was washed with saturated, aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solid was purified by recrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-4b5de1a79116477981c8fa45a39bbac2
出典データセット
uspto-grants-2008_05
特許番号
US07378427B2

反応ノート

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