Hydrochloric Acid → HCID 9815817, compound

HRID 985595Notes

Reaction equation

HRID 985595 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:8](=[C:9]([CH3:15])[C:10]=1[CH2:11][C:12]([CH3:14])=[CH2:13])[N:7](C=O)[CH2:6][CH2:5]2.Cl.[OH-].[Na+]>CO>[CH3:13][C:12]1([CH3:14])[O:1][C:2]2=[C:3]([CH3:18])[C:4]3[CH2:5][CH2:6][NH:7][C:8]=3[C:9]([CH3:15])=[C:10]2[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22506833HCID 22506833, compound

Product 1

HCID 9815817HCID 9815817, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2,3-Dihydro-5-hydroxy-4,7-dimethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (491 mg, 2.0 mmol) was dissolved in methanol (6 ml). To the solution was added concentrated hydrochloric acid (6 ml) and stirred for 3 hours with heating under reflux. The reaction mixture was cooled to 0° C., made weakly basic with 12N sodium hydroxide, and extracted with ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) and crystallized from hexane to obtain 330 mg of the title compound.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-55d24c367fa24f3aa5273c22fb9dd7a7
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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