Hydrochloric Acid → 6-Methoxy-1-methyl-1H-indole-3-carbaldehyde

HRID 1976723

Reaction equation

HRID 1976723 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:16]I.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][N:9]2[CH3:16])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

Product 1

HCID 13820106-Methoxy-1-methyl-1H-indole-3-carbaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxy-1H-indole-3-carboxaldehyde (1.65, 9.4 mm) in DMF (10 mL) was cooled to 0° C., and treated with NaH(11.3 mm). After stirring at room temperature for 1 hour, the mixture was cooled to 0° C., treated with CH3I (0.7 mL, 11.3 mm), then allowed to warm to room temperature overnight. After pouring into H2O (200 mL), the mixture was acidified with HCl and extracted with EtOAc (100 mL×2). The combined organic fractions were dried over MgSO4, filtered and evaporated to afford 6-methoxy-1-methyl-1H-indole-3-carboxaldehyde (1.78 g, 99%).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. temperatureto warm to room temperature overnight
  3. extractionextracted with EtOAc (100 mL×2)
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c70c54f8e082415f908c58c41ed3a9c5
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Linked notes

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