Water → 5-chloro-1H-indole-3-carbaldehyde

HRID 1606502Notes

Reaction equation

HRID 1606502 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.O.CN(C)[CH:19]=[O:20]>>[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:19]=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 871105-Chloroindole

Product 1

HCID 27953745-chloro-1H-indole-3-carbaldehyde

Conditions

Temperature
20 °C

Procedure

18.5 g (0.12 mole) of phosphorus oxychloride are added to 75 ml of dry dimethylformamide at 5°C. 15.15 g (0.1 mole) of 5-chloroindole dissolved in 30 ml of dry dimethylformamide are then added at 5°C. This is stirred for 30 minutes at 20°C, then for 30 minutes at 40°C. 240 ml of water followed by 72 ml of 40% soda are then quickly added. The yellow solution obtained is maintained at 40°-45°C for one hour. After 11/2 hours stirring at ambient temperature the precipitate formed is filtered off and recrystallised from ethyl alcohol.

Workup

  1. additionare then added at 5°C
  2. waitfor 30 minutes at 40°C
  3. additionare then quickly added
  4. customThe yellow solution obtained
  5. temperatureis maintained at 40°-45°C for one hour
  6. stirringAfter 11/2 hours stirring at ambient temperature the precipitate
  7. customformed
  8. filtrationis filtered off
  9. customrecrystallised from ethyl alcohol

Sources & evidence

ORD record
ord-e65b93cdae3440b3996aa8977cc1a875
Source dataset
uspto-grants-1976_04
Patent number
US03953442

Reaction notes

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