Sodium Hydroxide → HCID 19813411, compound

HRID 467121Notes

Reaction equation

HRID 467121 reaction equation
C([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=2)[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([CH3:25])[NH:8][C:7]=1[CH3:26])=[O:5])C.[OH-].[Na+].C(Cl)(Cl)Cl.CO>C(O)C>[C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=2)[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([CH3:25])[NH:8][C:7]=1[CH3:26])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 9950430HCID 9950430, compoundHCID 21584188Chloroform methanol

Product 1

HCID 19813411HCID 19813411, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 80 ml of ethyl alcohol was dissolved 7.5 g (0.02 mol) of 3,5-diethoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine obtained in Example 2. Thereto was added 20 ml of 5N sodium hydroxide. After stirring for 24 hours at room temperature, the mixture was reacted further for 30 hours at 40°-45° C. After completing the reaction, the reaction solution was distilled away under reduced pressure. Water and chloroform were added to the residue, and a water layer was collected. The water layer was acidified with concentrated hydrochloric acid to give precipitate. The precipitate was purified by subjecting to silica gel column chromatography [eluent: chloroform-methyl alcohol (100 : 5)]to give 1.5 g of the desired compound (yield: 23.1%).

Workup

  1. customthe mixture was reacted further for 30 hours at 40°-45° C
  2. customthe reaction
  3. distillationthe reaction solution was distilled away under reduced pressure
  4. additionWater and chloroform were added to the residue
  5. customa water layer was collected
  6. customto give precipitate
  7. customThe precipitate was purified

Sources & evidence

ORD record
ord-25057f706b2d4277a92a0efdd377e59e
Source dataset
uspto-grants-1992_10
Patent number
US05158963

Reaction notes

Loading…