Acetyl chloride → 10-Fluoro-imidazo[1,2-f]phenanthridine

HRID 2176358Notes

Reaction equation

HRID 2176358 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[C:13]1[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]1)=[N:7][C:6]=2[NH2:16].[C:17](Cl)(=O)[CH3:18].C(=O)(O)[O-].[Na+]>O.C(O)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:7]([CH:17]=[CH:18][N:16]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 112528289-Fluoro-6-phenanthridinamine

Product 1

HCID 5816243310-Fluoro-imidazo[1,2-f]phenanthridineYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

9-Fluoro-6-Phenanthridinamine (0.8 g, 3.7 mmol), and a 50% solution of acetyl chloride (0.4 g, 5.66 mmol) in water containing sodium bicarbonate (0.6 g, 7.54 mmol) was dissolved in isopropyl alcohol (25 mL). The reaction mixture was refluxed for 17 hours under a nitrogen pad. The reaction mixture was cooled to room temperature and the precipitate vacuum filtered and washed with methylene chloride. The crude product was purified by column chromatography using a 1:1 ratio of ethyl acetate and hexanes as the eluants followed by distillation to give 10-fluoro-imidazo[1,2-f]phenanthridine) (0.46 g, 52% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hours under a nitrogen pad
  2. filtrationthe precipitate vacuum filtered
  3. washwashed with methylene chloride
  4. customThe crude product was purified by column chromatography
  5. distillationfollowed by distillation

Sources & evidence

ORD record
ord-11f0e822ff8548869bab124ef671b4dc
Source dataset
uspto-grants-2015_06
Patent number
US09065063B2

Reaction notes

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