Indole → Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)

HRID 247552Notes

Reaction equation

HRID 247552 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CN(C)[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>O.CCOCC>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[O:21])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81713N,N-dimethyl-p-methoxybenzamide

Product 1

HCID 211017Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)Yield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.6 g of indole and 8.6 g of N,N-dimethylanisamide were added to 2.6 ml of phosphorus oxychloride. The mixture was heated at 80°-85° C. for 3 hours. After cooling,50 ml of ether was added to the mixture. The reaction mixture was then poured into water and pH value was adjusted to 10 with aqueous solution of sodium hydroxide. The resulting precipitate was filtered out and then recrystallized from ethanol to obtain compound 1 in the form of white crystals. (Yield: 56%)

Workup

  1. temperatureThe mixture was heated at 80°-85° C. for 3 hours
  2. temperatureAfter cooling
  3. filtrationThe resulting precipitate was filtered out
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6025311c4c8c4182b0f8ff44a0e8297d
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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