Benzenamine, 4-propoxy- → HCID 13938654, compound

HRID 2309411Notes

Reaction equation

HRID 2309411 reaction equation
[CH2:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH3:3].Br[CH:13]([CH3:25])[C:14]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=1)=O>>[OH:23][C:19]1[C:18]([CH3:24])=[CH:17][C:16]([C:14]2[NH:9][C:8]3[C:10]([C:13]=2[CH3:25])=[CH:11][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[CH:6][CH:7]=3)=[CH:21][C:20]=1[CH3:22]

Participants

3

Reactant 2

HCID 78221Benzenamine, 4-propoxy-HCID 20185248HCID 20185248, compound

Product 1

HCID 13938654HCID 13938654, compound

Procedure

3 g of 4-n-propoxyaniline and 2.56 g of 4-(2-bromo-1-oxopropyl)-2,6-dimethylphenol were heated at 150° C. for 40 minutes in a stream of nitrogen. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography, and recrystallized from ether-hexane to give 2-(4-hydroxy-3,5-dimethylphenyl)-3-methyl-5-n-propoxyindole.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was purified by silica gel column chromatography
  3. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-135e2e524f87402b98bd39f9210a7201
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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