2-Chloroethanol → 3-(p-methoxybenzoyl)-N-(2-hydroxyethyl)indole

HRID 247558Notes

Reaction equation

HRID 247558 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.Cl[CH2:21][CH2:22][OH:23]>CN(C)C=O.C[O-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:21][CH2:22][OH:23])[CH:10]=2)=[O:8])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 211017Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)

Product 1

HCID 136694973-(p-methoxybenzoyl)-N-(2-hydroxyethyl)indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
110 °C

Procedure

5 g of 3-(p-methoxybenzoyl)indole were dissolved in 30 ml of dimethylformamide containing 1.3 g of sodium methoxide. 1.93 g of 2-chloroethanol was added to the solution followed by stirring at 110° C. for 1 hour. The solution was concentrated under reduced pressure and was extracted with 100 ml of chloroform and 50 ml of water. After evaporating the organic layer to dryness, the residue was recrystallized from ethanol to give 3-(p-methoxybenzoyl)-N-(2-hydroxyethyl)indole (compound 21). (Yield: 51%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. extractionwas extracted with 100 ml of chloroform and 50 ml of water
  3. customAfter evaporating the organic layer to dryness
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-957b8c96f7994914a1055b400eb8ea7d
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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