Dimethylformamide → 5-Benzyl-3-formylindole

HRID 1720065Notes

Reaction equation

HRID 1720065 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].CN([CH:27]=[O:28])C>O>[CH2:6]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:27]=[O:28])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 124528915-Benzyl-1H-indole

Product 1

HCID 224199495-Benzyl-3-formylindoleYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Freshly distilled POCl3 (0.122 ml) was added dropwise to cooled (ice bath) dry DMF (0.4 ml). The mixture was stirred 0.5 h at 0° C., then a solution of 5-benzylindole (0.24 g, 1.2 mmol) in DMF (0.14 ml) was added dropwise, during which time the temperature was maintained below 10° C. Once the solution was well mixed, the temperature was brought to 35° C. The syrup was stirred efficiently at this temperature for 1 h. At the end of the reaction period 0.4 g of crushed ice was added to the paste with careful stirring. The cherry-red solution was transferred with H2O (0.13 ml) to a flask containing 0.28 g of crushed ice. A solution NaOH (0.53 g, 13 mmol) in H2O (1.4 ml) was added dropwise; the suspension was heated to reflux, allowed to cool to room temperature, and was placed in a refrigerator overnight the precipitate was collected by filtration, washed well with H2O and air-dried to provide 0.15 g (56%) of 5-benzyl-3-formylindole.

Workup

  1. temperaturewas maintained below 10° C
  2. additionOnce the solution was well mixed
  3. customwas brought to 35° C
  4. stirringThe syrup was stirred efficiently at this temperature for 1 h
  5. additionwas added to the paste with careful stirring
  6. temperaturethe suspension was heated
  7. temperatureto reflux
  8. temperatureto cool to room temperature
  9. customwas placed in a refrigerator overnight
  10. filtrationwas collected by filtration
  11. washwashed well with H2O
  12. customair-dried

Sources & evidence

ORD record
ord-d81b82177d7342e3b779b4fb0538a2c8
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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