Hydrochloric Acid → 3-(p-Hydroxy)benzoyl indole

HRID 247553Notes

Reaction equation

HRID 247553 reaction equation
C[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.N1C=CC=CC=1.Cl>>[OH: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)[NH:11][CH:10]=2)=[O:8])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 211017Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)HCID 10176127Pyridinium chloride

Product 1

HCID 30626713-(p-Hydroxy)benzoyl indole

Procedure

1 g of compound 1 and 3 g of pyridine hydrochloride were heated at 215° C. for 1 hour in a nitrogen atmosphere. After the mixture was cool,1.5 N hydrochloric acid was added thereto and then the supernatant was removed by centrifugation. The precipitate was dissolved in methanol which contains 10% of aqueous solution of sodium hydroxide, followed by filtering out the resulting precipitate. The obtained solution was acidified to give a crude product. The crude product was recrystallized from ethyl acetate to give 3-(p-hydroxybenzoyl)indole (compound 3). (Yield: 66%).

Workup

  1. temperatureAfter the mixture was cool
  2. customthe supernatant was removed by centrifugation
  3. dissolutionThe precipitate was dissolved in methanol which
  4. filtrationby filtering out the resulting precipitate
  5. customto give a crude product
  6. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f469414041a84f208baac4b6b4640a13
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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