Hydrochloric Acid → HCID 85905916, compound

HRID 1351947Notes

Reaction equation

HRID 1351947 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C:16]([OH:18])=[O:17])=[O:5])[CH3:2].Cl.[CH3:22]O>>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C:16]([O:18][CH3:22])=[O:17])=[O:5])[CH3:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 23071144HCID 23071144, compound

Product 1

HCID 85905916HCID 85905916, compoundYield 77%

Procedure

To a solution of (7-((diethylamino)carbonyl)-1H-indol-3-yl)acetic acid (2.38 g, 8.68 mmol) in methanol (10 mL) is added a 10% hydrogen chloride solution in methanol (30 mL) under nitrogen atmosphere, and the mixture is refluxed for 30 minutes. The reaction solution is cooled to room temperature, and the solvent is distilled off. To the residue is added chloroform, and the mixture is washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is removed by distillation, and the resultant crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→ethyl acetate) to give methyl (7-((diethylamino)carbonyl)-1H-indol-3-yl)acetate (1.93 g, yield: 77%).

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. distillationthe solvent is distilled off
  3. additionTo the residue is added chloroform
  4. washthe mixture is washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent is removed by distillation
  7. customthe resultant crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-9ff0d528a7cc4ae78f7752659506ae85
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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