Indole → Indole-3-Carboxaldehyde

HRID 1533099Notes

Reaction equation

HRID 1533099 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.CN([CH:18]=[O:19])C>>[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:18]=[O:19])=[CH:7]1

Participants

4

Reactant 3

HCID 798IndoleHCID 6228DimethylformamideHCID 24813Phosphorus oxychloride

Product 1

HCID 10256Indole-3-CarboxaldehydeYield 90%

Conditions

Temperature
0 °C

Procedure

To a 500 mL round bottom flask containing 250 mL of DMF at 0° C. was added 105 mL (1.12 mol) of phosphorous oxychloride dropwise via an addition funnel. The reaction mixture was stirred for 30 min at 0° C. and then indole (0.51 mol) was added as a solid. The reaction mixture was heated to 80° C. for 6 h and then cooled in an ice bath. The cold solidified reaction was quenched with water (Q2 L) until all the solid had dissolved. The solution was kept cool and the pH was adjusted to ˜11 by the addition of 50% NaOH. The precipitate was filtered and washed with water. The filter cake was dried in vacuo in the presence of P2O5 to yield crude indole-3-carboxaldehyde (90-95% yield).

Workup

  1. temperatureThe reaction mixture was heated to 80° C. for 6 h
  2. temperaturecooled in an ice bath
  3. customreaction
  4. customwas quenched with water (Q2 L) until all the solid
  5. dissolutionhad dissolved
  6. temperatureThe solution was kept cool
  7. additionthe pH was adjusted to ˜11 by the addition of 50% NaOH
  8. filtrationThe precipitate was filtered
  9. washwashed with water
  10. dry with materialThe filter cake was dried in vacuo in the presence of P2O5

Sources & evidence

ORD record
ord-ad22ad75f4364accb28e61351a9c61c8
Source dataset
uspto-grants-2001_03
Patent number
US06207679B1

Reaction notes

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