Iodoethane → HCID 19598472, compound

HRID 51202Notes

Reaction equation

HRID 51202 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[NH:7]1[C:15]2[C:10](=C[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.[CH2:16](I)[CH3:17]>>[CH2:16]([N:7]1[C:15]2[C:10](=[C:1]([OH:4])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1)[CH3:17]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 10328IndolineHCID 11430Potassium Carbonate

Product 1

HCID 19598472HCID 19598472, compoundYield 23%

Procedure

4-Hydroxyindole was reduced with sodium cyanoborohydride and acetic acid to give 4-hydroxy, dihydroindole. A mixture of ethyl iodide (40 ml), potassium carbonate (1.09 gm, 7.8 mmole) and 4-hydroxy, dihydroindole (1.06 gm, 7.8 mmole) was refluxed for 2 hr. Excess ethyl iodide was evaporated under vacuum, water was added (10 ml) and the product was extracted with dichloromethane. Silica gel chromatography gave N-ethyl4-hydroxy-dihydroindole (0.30 gm, 23% yield) as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 2 hr
  2. customExcess ethyl iodide was evaporated under vacuum, water
  3. additionwas added (10 ml)
  4. extractionthe product was extracted with dichloromethane

Sources & evidence

ORD record
ord-0755820e9649490c8c0c160c8b18399c
Source dataset
uspto-grants-2004_03
Patent number
US06713622B1

Reaction notes

Loading…