Hydrochloric Acid → HCID 9837328, compound

HRID 1743399Notes

Reaction equation

HRID 1743399 reaction equation
[OH:1][C:2]1[C:3]([CH2:15][C:16]([CH3:18])=[CH2:17])=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[N:7](C=O)[CH2:6][CH2:5]2.Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO.O>[CH3:17][C:16]1([CH3:18])[O:1][C:2]2[C:3](=[C:4]3[C:8](=[C:9]([CH3:12])[C:10]=2[CH3:11])[NH:7][CH2:6][CH2:5]3)[CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22238067HCID 22238067, compound

Product 1

HCID 9837328HCID 9837328, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2,3-dihydro-5-hydroxy-6,7-dimethyl-4-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (1.23 g, 5.0 mmol) in methanol (4 mL) was added concentrated hydrochloric acid (2 mL)-methanol (1 mL) solution, and the mixture was heated to reflux for 2 hours under the nitrogen atmosphere. The reaction mixture was added to a mixture of sodium bicarbonate (3.02 g, 35.9 mmol) in water (10 mL)-ethyl acetate (10 mL) to neutralize, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over magnesium sulfate, treated with active carbon, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 497 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours under the nitrogen atmosphere
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with active carbon
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d03e7b3b2c8546a9959deb43b33012e6
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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