Hydrochloric Acid → HCID 13490375, compound

HRID 485341Notes

Reaction equation

HRID 485341 reaction equation
C([O:3][C:4]([CH2:6][CH:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1)[CH3:8])=[O:5])C.O.[OH-].[Na+].[ClH:27]>CO.O1CCCC1>[ClH:27].[C:4]([CH2:6][CH:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1)[CH3:8])([OH:5])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53920417HCID 53920417, compound

Product 1

HCID 13490375HCID 13490375, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.66 g of 3-(3-ethoxycarbonyl-2-propyl)-N-(3-pyridyl)indole in 15 ml of methanol and 15 ml of water containing 0.7 g of sodium hydroxide is stirred at room temperature for 18 hours, refluxed for 15 minutes, cooled and evaporated. The residue is redissolved in 25 ml of water, neutralized to pH 6 with 1.44 ml of concentrated hydrochloric acid. The resulting oil is extracted into methylene chloride and the extract is dried over sodium sulfate. Filtration and evaporation gives an oil which is redissolved in 5 ml of tetrahydrofuran and treated with 0.55 ml of concentrated hydrochloric acid. The resulting semi-solid is crystallized from methanol-ether to yield 3-(3-carboxy-2-propyl)-N-(3-pyridyl)indole hydrochloride, m.p. 205°-207°.

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe residue is redissolved in 25 ml of water
  5. extractionThe resulting oil is extracted into methylene chloride
  6. dry with materialthe extract is dried over sodium sulfate
  7. filtrationFiltration and evaporation
  8. customgives an oil which
  9. customThe resulting semi-solid is crystallized from methanol-ether

Sources & evidence

ORD record
ord-ead98a00ff91480d9fb66fb25bf51652
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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