Hydrochloric Acid → Methyl 1-isopropyl-1H-indole-6-carboxylate

HRID 342065Notes

Reaction equation

HRID 342065 reaction equation
CO[CH:3](OC)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=1[NH:15][CH:16]([CH3:18])[CH3:17].Cl>CO>[C:11]([C:8]1[CH:7]=[C:6]2[C:5]([CH:4]=[CH:3][N:15]2[CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1)([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 193540554-Carbomethoxy-2-(N-2-propylamino)phenylacetaldehyde dimethylacetal

Product 1

HCID 10608809Methyl 1-isopropyl-1H-indole-6-carboxylateYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Carbomethoxy-2-(N-2-propylamino)phenylacetaldehyde dimethylacetal (3.7 g, 13.15 mmole) was refluxed with 100 mL of 1N hydrochloric acid in methanol for 1 h. The solution was concentrated and the residue dissolved in 50 mL of ethyl acetate, washed with saturated sodium bicarbonate solution, dried organic layer over magnesium sulfate and evaporated to give 2.78 g of 6-carbomethoxy-1-(2-propyl)indole.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in 50 mL of ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution, dried organic layer over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8f100ba8036741fab008aba098d47ad9
Source dataset
uspto-grants-1999_01
Patent number
US05856517

Reaction notes

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