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3-Chloro-1-propanol → 3-[p-(3-Hydroxypropoxy)benzoyl]indole

HRID 247559
Notes
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Reaction equation

HRID 247559 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][CH2:22][OH:23]>CN(C)C=O.C[O-].[Na+]>[OH:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 123133-Chloro-1-propanolHCID 30626713-(p-Hydroxy)benzoyl indole

Product 1

HCID 136694983-[p-(3-Hydroxypropoxy)benzoyl]indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
110 °C

Procedure

5 g of 3-(p-hydroxybenzoyl) indole were dissolved in 50 ml of dimethylformamide containing 2.28 g of sodium methoxide. 4.0 g of 3-chloropropanol was added to the solution followed by stirring at 110° C. in oil bath for 3 hours. After cooling, the solution was concentrated and extracted with 100 ml of ethyl acetate and 50 ml of water. The organic layer obtained was concentrated, and then the residue was purified by column chromatography on silica gel. Crude product was recrystallized from ethyl acetate to give 3-[p-(3-hydroxypropoxy)benzoyl]indole (compound 23) in the form of white needle crystals. (Yield: 30.5%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated
  3. extractionextracted with 100 ml of ethyl acetate and 50 ml of water
  4. customThe organic layer obtained
  5. concentrationwas concentrated
  6. customthe residue was purified by column chromatography on silica gel
  7. customCrude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3a41a8799db94481aee317a672da15a7
Source dataset
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04708961

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes