Hydrochloric Acid → HCID 13362120, compound

HRID 1462622Notes

Reaction equation

HRID 1462622 reaction equation
[NH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)N.Cl.[C:15]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=O)[CH2:16][CH3:17].[OH-].[Na+].[CH2:27](O)[CH3:28]>O>[CH3:17][C:16]1[C:13]2[C:3](=[CH:4][CH:5]=[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:27][CH3:28])=[O:10])[CH:12]=2)[NH:1][C:15]=1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 740741-(3-Pyridyl)propan-1-oneHCID 155913643-(4-Hydrazinylphenyl)propanoic acid

Product 1

HCID 13362120HCID 13362120, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of p-hydrazinohydrocinnamic acid (Manske and Kulka, J. Can. Res., 25B: 376 (1947), 4.50 g) in 50 ml of absolute ethanol under nitrogen at room temperature was added while stirring 10 ml of a saturated ethanolic hydrogen chloride solution. A solution resulted in approximately 5 minutes. To the red-orange solution was added 3-propionylpyridine (3.37 g, 0.025 mole), the reaction mixture was heated to reflux and maintained at reflux for 18 hours. The resulting solution was cooled in an ice-water bath and the resulting yellow crystals of ethyl 3-methyl-2-(3-pyridyl)indole-5-propionate hydrochloride were collected, m.p. 249°-51°. The free base, ethyl 3-methyl-2-(3-pyridyl)indole-5-propionate was prepared by suspending the hydrochloride salt in water, basifying with 3N sodium hydroxide and extracting with ether.

Workup

  1. additionwas added
  2. customA solution resulted in approximately 5 minutes
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. temperatureat reflux for 18 hours
  7. temperatureThe resulting solution was cooled in an ice-water bath
  8. customthe resulting yellow crystals of ethyl 3-methyl-2-(3-pyridyl)indole-5-propionate hydrochloride were collected
  9. extractionextracting with ether

Sources & evidence

ORD record
ord-7fe458e1e8d94fc893de98dcc598cf71
Source dataset
uspto-grants-1984_07
Patent number
US04460777

Reaction notes

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