Indole → Indole-3-Carboxaldehyde

HRID 1843917Notes

Reaction equation

HRID 1843917 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O=P(Cl)(Cl)Cl.[CH2:15]([O:17]C(=O)C)C>CN(C=O)C.CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:15]=[O:17])=[CH:2]1

Participants

6

Reactant 3

HCID 798IndoleHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychloride

Product 1

HCID 10256Indole-3-CarboxaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

1H-Indole (10 g, 85.360 mmol) in DMF (10 mL) was added dropwise to a stirred solution of POCl3 (8.67 mL, 93.896 mmol) in DMF over a period of 10 minutes at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (40% ethylacetate in hexane). The reaction mixture was quenched with chilled water, followed by the addition of aqueous NaOH solution and refluxed at 100° C. for 15 minutes. The reaction mixture was cooled to room temperature and maintained at 0° C. overnight. The precipitate formed was collected, washed with water and dried to afford 11.6 g of the product (94% yield).

Workup

  1. customThe reaction mixture was quenched with chilled water
  2. additionfollowed by the addition of aqueous NaOH solution
  3. temperaturerefluxed at 100° C. for 15 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. temperaturemaintained at 0° C. overnight
  6. customThe precipitate formed
  7. customwas collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-d9310c84b54c42c299072ec190f3b3ef
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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