Ammonium Hydroxide → 8-Fluoro-6-methylphenanthridine

HRID 2224630Notes

Reaction equation

HRID 2224630 reaction equation
[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

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 16679975HCID 16679975, compound

Product 1

HCID 224823738-Fluoro-6-methylphenanthridineYield 94%

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4b5de1a79116477981c8fa45a39bbac2
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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