Hydrochloric Acid → Indole

HRID 2393772Notes

Reaction equation

HRID 2393772 reaction equation
C[Si](C)(C)[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.C(OC(C)C)(=O)C.O>CO>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7915Isopropyl AcetateHCID 10921317Trimethylsilyl indole

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the 2-trimethylsilyl indole product of Example 1 (0.50 g, 2.6 mmol) in 5 mL methanol was treated with 2.5N HCl (2.11 mL, 5.2 mmol) and the reaction mixture was aged at room temperature for 2 h. Isopropyl acetate (50 mL) and water (10 mL). were then added. The layers were separated and the organic layer was concentrated under vacuum. The residual oil was chromatographed over silica gel to afford the indole as a white solid.

Workup

  1. additionwere then added
  2. customThe layers were separated
  3. concentrationthe organic layer was concentrated under vacuum
  4. customThe residual oil was chromatographed over silica gel

Sources & evidence

ORD record
ord-d664bfb7f20d43d6a7fe4399dd981ef1
Source dataset
uspto-grants-1998_09
Patent number
US05808064

Reaction notes

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