Phosphorus oxychloride → HCID 86673690, compound

HRID 1845976Notes

Reaction equation

HRID 1845976 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5](O)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.P(Cl)(Cl)([Cl:19])=O>CN(C)C=O>[Cl:19][C:5]1[N:6]=[C:7]2[C:12](=[C:13]3[C:4]=1[CH:3]=[C:2]([F:1])[CH:15]=[CH:14]3)[CH:11]=[CH:10][CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517107HCID 178517107, compound

Product 1

HCID 86673690HCID 86673690, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 8-fluorophenanthridin-6-ol (Example 2a, 0.15 g, 0.69 mmol) in phosphorus oxychloride (1.06 g, 0.65 mL, 6.9 mmol) was added dimethylformamide (5 mg, 5 μL), and the reaction mixture was warmed to 80° C. and stirred under nitrogen for 3 h. The reaction mixture was cooled to room temperature and evaporated under reduced pressure. The residue was triturated with hexane, and the resulting solid isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 95% yield) which was used without additional purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated under reduced pressure
  3. customThe residue was triturated with hexane
  4. customthe resulting solid isolated by vacuum filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-cfb0c315238b44f3a6517bf653ac700e
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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