Dimethylformamide → HCID 11206654, compound

HRID 1985739Notes

Reaction equation

HRID 1985739 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:10])C=O.[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][C:17](=[O:21])N2)=C[CH:13]=1.C(Cl)(=O)C([Cl:25])=O>ClCCl.O>[Cl:25][C:10]1[NH:7][C:6]2[C:15]([C:16]=1[CH:17]=[O:21])=[CH:19][CH:20]=[C:12]([Cl:11])[CH:13]=2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 65578Oxalyl chlorideHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 11206654HCID 11206654, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, 27 ml (292 mmol) of phosphorus oxychloride were added dropwise at 0° C. to 28 ml (366 mmol) of N,N-dimethylformamide in 190 ml of dichloromethane. The mixture was stirred for 2 h at ambient temperature. It was cooled to 0° C. and 24.5 g (146 mmol) of 6-chloro-1,3-dihydro-2H-indol-2-one were added in small portions. The mixture was stirred for 4 h at ambient temperature. It was cooled to 0° C. and 12.7 ml (146 mmol) of oxalyl chloride were added. Next, it was stirred for 12 h at ambient temperature. The mixture was cooled and 250 ml of water were added. The organic phase was decanted and washed with water (3 times). A solid precipitated from the organic phase. It was recovered by filtration and dried under reduced pressure in the presence of phosphorus pentoxide. The aqueous phases were combined and stirred for around 7 h. A solid precipitated from the aqueous phase. It was recovered by filtration and it was also dried under reduced pressure in the presence of phosphorus pentoxide. The two precipitates were combined and 16 g of 2,6-dichloro-1H-indole-3-carbaldehyde were obtained in the form of a white/beige solid.

Workup

  1. temperatureIt was cooled to 0° C.
  2. stirringThe mixture was stirred for 4 h at ambient temperature
  3. temperatureIt was cooled to 0° C.
  4. stirringNext, it was stirred for 12 h at ambient temperature
  5. temperatureThe mixture was cooled
  6. customThe organic phase was decanted
  7. washwashed with water (3 times)
  8. customA solid precipitated from the organic phase
  9. filtrationIt was recovered by filtration
  10. dry with materialdried under reduced pressure in the presence of phosphorus pentoxide
  11. stirringstirred for around 7 h
  12. customA solid precipitated from the aqueous phase
  13. filtrationIt was recovered by filtration and it
  14. dry with materialwas also dried under reduced pressure in the presence of phosphorus pentoxide
  15. customThe two precipitates

Sources & evidence

ORD record
ord-b8d83d55c7d34cdbb25153fd38d47ac0
Source dataset
uspto-grants-2009_06
Patent number
US07547706B2

Reaction notes

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