Potassium Hydroxide → Indenolol

HRID 1704754Notes

Reaction equation

HRID 1704754 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.[OH-].[K+].Cl[CH2:14][CH:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19]>>[CH:18]([NH:17][CH2:16][CH:15]([OH:21])[CH2:14][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2)([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 126246123-Isopropylamino-2-hydroxy-1-chloropropaneHCID 149408631H-Inden-4-ol

Product 1

HCID 71955Indenolol

Procedure

To a solution of 0.44 g. of 4-hydroxyindene in 4 ml. of an aqueous 10% potassium hydroxide solution there was added 0.65 g. of 1-chloro-2-hydroxy-3-isopropylaminopropane. After stirring the resulting mixture at room temperature for 15 hours, the reaction mixture was extracted with ether, the ether extract was dried with anhydrous sodium carbonate and the ether was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using acetone as eluent, and 0.23 g. of white crystals of 4-(3-isopropylamino-2-hydroxypropoxy)indene was obtained.

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. extractionthe ether extract
  3. dry with materialwas dried with anhydrous sodium carbonate
  4. distillationthe ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7e1929aae31f4b1da5712f839eec7b72
Source dataset
uspto-grants-1978_11
Patent number
US04127675

Reaction notes

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