Hydrochloric Acid → 2-(4-Hydroxyphenyl)indole

HRID 1448699Notes

Reaction equation

HRID 1448699 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=O.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>[Cl-].[Zn+2].[Cl-]>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([C:2]2[NH:17][C:11]3[C:16]([CH:1]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20375259HCID 20375259, compound

Product 1

HCID 112872602-(4-Hydroxyphenyl)indoleYield 42.2%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

4-Hydroxyacetophenone phenylhydrazine (47 g.) was fused with 250 g. zinc chloride (10 min. at 180° C.), poured into 3 l. 0.3 HCl, heated and stirred for 1 hour on the steam bath, cooled to 0° and filtered. The precipitate was extracted with pet. ether and allowed to stand. 2-(p-hydroxyphenyl)indole (17 g., m. 224°-229°) was isolated. A well stirred mixture of 2-(p-hydroxyphenyl)indole (0.1 mole), iodoethane (0.1 mole) and sodium bicarbonate (0.12 mole) in 200 ml. of acetone was refluxed overnight, filtered and the acetone removed on the steambath. The isolated 2-(p-hydroxyphenyl)-1-ethylindole was reacted with 4-(2-bromoethoxy)-2,2,6,6-tetramethylpiperidine as in Example 1 to produce 4-{2-[4-(1-ethyl-2-indolyl)phenoxy]ethoxy}-2,2,6,6-tetramethylpiperidine.

Workup

  1. temperaturecooled to 0°
  2. filtrationfiltered
  3. extractionThe precipitate was extracted with pet. ether

Sources & evidence

ORD record
ord-9151567108574a459af1e03d3cc00d42
Source dataset
uspto-grants-1980_02
Patent number
US04187213

Reaction notes

Loading…