Dimethylformamide → HCID 86673689, compound

HRID 1845974Notes

Reaction equation

HRID 1845974 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12](O)=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1.P(Cl)(Cl)([Cl:19])=O.CN(C)C=O>>[Cl:19][C:12]1[N:13]=[C:14]2[C:5](=[C:6]3[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH:4]=[CH:3][C:2]([F:1])=[CH:15]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178517313HCID 178517313, compound

Product 1

HCID 86673689HCID 86673689, compoundYield 70%

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-fluorophenanthridin-6-ol (Example 1a, 1.58 g, 7.41 mmol) in phosphorus oxychloride (11.7 g, 7.1 mL, 76 mmol) was added dimethylformamide (0.34 g, 0.46 mmol), and the reaction mixture was warmed to 65° C. and stirred under nitrogen for 1 h. The reaction mixture was cooled to room temperature, followed by the careful addition of ice to the reaction mixture. The mixture was stirred for 20 min, and the extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide the title compound (1.2 g, 70% yield), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionfollowed by the careful addition of ice to the reaction mixture
  3. stirringThe mixture was stirred for 20 min
  4. extractionthe extracted with ethyl acetate
  5. washThe resulting organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-442548be960848cebd6e47948480b43f
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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