Citric Acid → 2-Chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 618100

Reaction equation

HRID 618100 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.CI.[H-].[Na+].[C:17](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CS(C)=O>[Cl:1][C:2]1[N:3]([CH3:17])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloroindole-3-carboxaldehyde (2.69 g) and methyl iodide (4.26 g) were dissolved in a mixed solvent of tetrahydrofuran (25 ml) and dimethylsulfoxide (25 ml), and sodium hydride (0.66 g, 60% mineral oil dispersion) was added thereto at 0° C. A 10% aqueous solution of citric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then a saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was washed with hexane (30 ml) to give 2-chloro-1-methylindole-3-carboxaldehyde (2.54 g).

Workup

  1. additionwas added
  2. customat 0° C
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated saline, and dried over anhydrous magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. washthe residue was washed with hexane (30 ml)

Sources & evidence

ORD record
ord-ab7790e956c94d0096d42c63e6468f5d
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

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