Ammonium Hydroxide → 8-Fluoro-6-methylphenanthridine

HRID 968679Notes

Reaction equation

HRID 968679 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-methylphenanthridine

Conditions

Temperature
120 °C

Procedure

The N-(4′-fluorobiphenyl-2-yl)acetamide (18.5 g, 80.7 mmol) was mixed with polyphosphoric acid (250 g) and heated at 120° C. with vigorous stirring for 48 hours. The hot reaction mixture was poured onto ice and stirred vigorously until homogeneous. Ammonium hydroxide (28-30%, aqueous) was added until the pH was greater than eight. A white precipitate was filtered, dissolved in ethyl acetate (250 mL), and re-filtered. The combined filtrate was washed with a saturated, aqueous, sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to a brown solid. The brown solid was purified by crystallization from a mixture of ethyl acetate-hexane to yield the title compound as a white, crystalline solid (15.9 g, 94%), m.p. 92-93° C.; MS [(+ESI), m/z]: 212 [M+H]+;

Workup

  1. additionThe hot reaction mixture was poured onto ice
  2. stirringstirred vigorously until homogeneous
  3. filtrationA white precipitate was filtered
  4. dissolutiondissolved in ethyl acetate (250 mL)
  5. filtrationre-filtered
  6. washThe combined filtrate was washed with a saturated, aqueous, sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a brown solid
  10. customThe brown solid was purified by crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-0758d7fd00fb4e1a8f9859931cd05179
Source dataset
uspto-grants-2007_12
Patent number
US07304073B2

Reaction notes

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