Dimethylformamide → 1,4,6-Trimethyl-1H-indole-3-carbaldehyde

HRID 2175184Notes

Reaction equation

HRID 2175184 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[CH:4]=[CH:3]1.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.CN([CH:25]=[O:26])C>>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([CH:25]=[O:26])=[CH:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4432411Diphosphoryl tetrachlorideHCID 13411053HCID 13411053, compound

Product 1

HCID 534339461,4,6-Trimethyl-1H-indole-3-carbaldehyde

Procedure

A solution of 1,4,6-trimethyl-1H-indole (800 mg, 5 mmol) in DMF (0.9 mL) was cooled to 5° C. under nitrogen. The pyrophosphoryl chloride (1.4 mL, 10 mmol) was then slowly introduced. Upon complete addition the cooling bath was removed and the reaction was allowed to warm to ambient temperature. After a total of 45 minutes the reaction was cooled to 5° C. and slowly quenched with 2N NaOH. The pH was adjusted to 8. The solid that precipitate out from the solution was collected by filtration and was washed with water. The remaining white solid was dried in the oven and was confirmed to be the title compound (875 mg, 93%).

Workup

  1. additionUpon complete addition the cooling bath
  2. customwas removed
  3. temperatureAfter a total of 45 minutes the reaction was cooled to 5° C.
  4. customslowly quenched with 2N NaOH
  5. filtrationThe solid that precipitate out from the solution was collected by filtration
  6. washwas washed with water
  7. customThe remaining white solid was dried in the oven

Sources & evidence

ORD record
ord-f6aa131a51cf4c0e9c7d24e49de30bef
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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