Hydrochloric Acid → HCID 20400794, compound

HRID 1980852Notes

Reaction equation

HRID 1980852 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25]N)=[CH:21][CH:20]=1.Cl.[CH2:28](O)[CH3:29]>>[ClH:18].[Cl:18][C:19]1[CH:24]=[C:23]2[C:22](=[CH:21][CH:20]=1)[NH:25][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:28][CH3:29])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702Ethanol2×HCID 70624(4-Chlorophenyl)hydrazineHCID 10889878HCID 10889878, compound

Product 1

HCID 20400794HCID 20400794, compound

Procedure

A mixture of 9.60 g of 7-nicotinoylheptanoic acid and 7.34 g of 4-chlorophenylhydrazine in 100 ml of ethanol is stirred and refluxed under nitrogen overnight. The reaction mixture is concentrated in vacuo to give a gum, which is suspended in 100 ml of ethanol, treated with 40 ml of 6N ethanolic hydrogen chloride, and refluxed under nitrogen for 22 hours. The suspension is cooled and an additional 50 ml of 6N ethanolic hydrogen chloride is added. Refluxing is resumed and continued for about 20 hours. The suspension is cooled in an ice-water bath and filtered. The filtrate is concentrated in vacuo to give a partially solid residue, which is triturated with ether-ethanol (10:1) and the yellow solid formed is collected to give 5-chloro-3-[5-(ethoxycarbonyl)pentyl]-2-(3-pyridyl)indole hydrochloride, m.p. 141°-145°.

Workup

  1. temperaturerefluxed under nitrogen overnight
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customto give a gum, which
  4. temperaturerefluxed under nitrogen for 22 hours
  5. temperatureThe suspension is cooled
  6. temperatureRefluxing
  7. temperatureThe suspension is cooled in an ice-water bath
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated in vacuo
  10. customto give a partially solid residue, which
  11. customis triturated with ether-ethanol (10:1)
  12. customthe yellow solid formed
  13. customis collected

Sources & evidence

ORD record
ord-47a8a5903ab947df96c5ed0628f0fa41
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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