Dimethylformamide → 5-Methoxyindole-3-carbaldehyde

HRID 2303955Notes

Reaction equation

HRID 2303955 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[OH-].[Na+].CN(C)[CH:21]=[O:22]>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 138725-MethoxyindoleHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 827585-Methoxyindole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To stirred dimethylformamide is added dropwise phosphorus oxychloride. The mixture is stirred for 10 min and a solution of 5-methoxyindole in dimethylformamide is added dropwise. The mixture is heated to 40° C. for 45 min, cooled to room temperature and then treated with a solution of sodium hydroxide in water. The mixture is heated to 50° C. for 10 min, cooled to room temperature, poured onto crushed ice and filtered. The filter cake is recrystallised (methanol) to give the product as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe mixture is heated to 50° C. for 10 min
  3. temperaturecooled to room temperature
  4. additionpoured
  5. customonto crushed ice
  6. filtrationfiltered
  7. customThe filter cake is recrystallised (methanol)

Sources & evidence

ORD record
ord-e06a319054fe43a39464f7f5120001d7
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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