1,2-Dichlorobenzene → 4-allyl-5-hydroxy-N-(4-chlorophenyl)indole

HRID 342768Notes

Reaction equation

HRID 342768 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:9]=[CH:8]2)C=C.Cl[C:22]1[CH:27]=CC=C[C:23]=1Cl>>[CH2:27]([C:6]1[C:5]([OH:4])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[CH:22]=[CH2:23]

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 544104885-allyloxy-N-(4-chlorophenyl)indole

Product 1

HCID 541263834-allyl-5-hydroxy-N-(4-chlorophenyl)indole

Procedure

5-allyloxy-N-(4-chlorophenyl)indole (Step B; 1.4 g, 4.93 mmol) was refluxed in 20 mL 1,2-dichlorobenzene for 4 hours. The reaction mixture was cooled and immediately purified by flash chromatography on silica gel (gradient elution: hexane then 10% ethyl acetate/hexane) to provide the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customimmediately purified by flash chromatography on silica gel (
  3. washgradient elution

Sources & evidence

ORD record
ord-be17f69fb42547c5b995b590007c3d52
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

Loading…