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

HRID 378372Notes

Reaction equation

HRID 378372 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-ee653f7bebe748cdb1a83ef871bf4b78
Source dataset
uspto-grants-2000_02
Patent number
US06030994

Reaction notes

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