Hydrochloric Acid → HCID 19917171, compound

HRID 1464792Notes

Reaction equation

HRID 1464792 reaction equation
[CH2:1]([N:3]([CH2:13][C:14]1[CH:15]=[C:16](CC#N)[CH:17]=[CH:18][CH:19]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2].[OH-].[Na+].Cl.[C:26]([O:29]CC)(=[O:28])[CH3:27]>C(O)C.O>[CH2:1]([N:3]([CH2:13][C:14]1[CH:15]=[C:16]([CH2:27][C:26]([OH:29])=[O:28])[CH:17]=[CH:18][CH:19]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19916988HCID 19916988, compound

Product 1

HCID 19917171HCID 19917171, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

195 mg of the resulting nitrile compound was dissolved in 6 ml of ethanol, and a 3N aqueous solution (2ml) of sodium hydroxide was added. The mixture was refluxed for 3 hours, and then acidified with 1N hydrochloric acid. Ethyl acetate and water were added, and the organic layer separated was worked up in a customary manner. The product was purified by silica gel column chromatography [ethyl acetate / methanol=20/1] to give 176 mg of the captioned compound as a colorless oil.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customthe organic layer separated
  3. customThe product was purified by silica gel column chromatography [ethyl acetate / methanol=20/1]

Sources & evidence

ORD record
ord-6642444a7c7d4959b1a44df6bf5474c6
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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