Citric Acid → HCID 59030592, compound

HRID 1619194Notes

Reaction equation

HRID 1619194 reaction equation
[C:1]([C:3]1([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].[OH-].[K+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCOC(C)=O.CO>[O:13]=[C:6]1[CH2:7][CH2:8][C:3]([C:14]2[N:15]=[CH:16][CH:17]=[CH:18][N:19]=2)([C:1]#[N:2])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 68859189HCID 68859189, compound

Product 1

HCID 59030592HCID 59030592, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The crude methyl 5-cyano-2-oxo-5-(pyrimidin-2-yl)cyclohexanecarboxylate was completely dissolved in THF/MeOH (1/1, 8 mL) and the clear solution was treated with 1 M aqueous KOH (3.0 mL, 1.2 equiv.) and H2O (2.5 mL). After being refluxed for 24 h, The organic solvent was removed under reduced pressure. The concentrated reaction was diluted (H2O), neutralized (10% citric acid) and extracted (3×DCM). The combined organics were dried (Na2SO4) and concentrated under reduced pressure to provide 4-oxo-1-(pyrimidin-2-yl)cyclohexanecarbonitrile (333 mg, 1.66 mmol, 68% yield) as a yellow solid.

Workup

  1. temperatureAfter being refluxed for 24 h
  2. customThe organic solvent was removed under reduced pressure
  3. customThe concentrated reaction
  4. extractionextracted (3×DCM)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f5f0c5ce75f41c0bdcf0597410c8624
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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