Hydrochloric Acid → HCID 20400819, compound

HRID 1980847Notes

Reaction equation

HRID 1980847 reaction equation
[ClH:1].[C:2]1([NH:8]N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.Cl.[CH2:28](O)[CH3:29]>>[ClH:1].[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2[NH:8][C:2]3[C:7]([C:18]=2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:28][CH3:29])=[O:25])=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 60962Phenylhydrazine hydrochlorideHCID 10889878HCID 10889878, compound

Product 1

HCID 20400819HCID 20400819, compound

Procedure

A mixture of 10.32 g of phenylhydrazine hydrochloride and 16.8 g of 7-nicotinoylheptanoic acid in 750 ml of ethanol is heated at refux temperature for 6 hours. After cooling with an ice-water bath, 250 ml of ca 2N ethanolic hydrogen chloride is added and the mixture heated at reflux for 16 hours. The mixture is filtered and the filtrate is concentrated under reduced pressure. The crude product is triturated with petroleum ether and recrystallized from ethanol-ether to yield 2-(3-pyridyl)-3-[5-(ethoxycarbonyl)-pentyl]-indole hydrochloride, m.p. 145°-150°.

Workup

  1. temperatureis heated at refux temperature for 6 hours
  2. temperatureAfter cooling with an ice-water bath
  3. temperaturethe mixture heated
  4. temperatureat reflux for 16 hours
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe crude product is triturated with petroleum ether
  8. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-34aae48be2cb48cb810c5898ed9815fa
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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