HCID 19010007, compound → HCID 15148204, compound

HRID 1742134Notes

Reaction equation

HRID 1742134 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:21])=[C:5]([C:18]([O-:20])=[O:19])[CH:6]([CH3:17])[C:7]=1[C:8]([O:10]CC(C#N)C#N)=[O:9]>CC(C)=O.[OH-].[Na+].O>[CH3:21][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]([CH3:17])[C:5]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 1

HCID 19010007HCID 19010007, compound

Product 1

HCID 15148204HCID 15148204, compoundYield 88.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 12 0 ml of acetone containing 240 ml of 1N sodium hydroxide was dissolved 12 . 7 g of the dicyanoethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate obtained in (1) above, and the solution was stirred at a room temperature for 2 hours. After the reaction, the reaction mixture was diluted with 240 ml of water and washed twice with dichloromethane. The separated aqueous layer was rendered acidic (pH=1-2) with concentrated hydrochloric acid under ice-cooling and stirred for 3 hours- The thus formed crystal was collected by suction filtration. The filtrate was dried under reduced pressure to yield 4.55 g (yield: 54%) of 1,4-dihydro- 2,4,6-trimethyl-3,5-pyridinedicarboxylic acid as a pale yellows powder.

Workup

  1. customAfter the reaction
  2. washwashed twice with dichloromethane
  3. temperaturecooling
  4. stirringstirred for 3 hours- The thus formed crystal
  5. filtrationwas collected by suction filtration
  6. customThe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-f773b441fa354ddfb258a6929b15d89a
Source dataset
uspto-grants-1994_08
Patent number
US05336774

Reaction notes

Loading…