Acetic Acid → HCID 136168330, compound

HRID 1729058Notes

Reaction equation

HRID 1729058 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[CH2:10][CH2:11][CH3:12])=[C:4]([C:14]#[N:15])[N:3]=1.[OH-].[Na+].C(O)(=[O:20])C>CO.O>[CH2:10]([C:9]1[NH:15][C:14](=[O:20])[C:4]2[N:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[N:8]=1)[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 19013309HCID 19013309, compound

Product 1

HCID 136168330HCID 136168330, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 0.56 g (2.5 mol) of 2-chloro-5-(N-butyroyl)amino-6-cyano-pyridine in 5 ml of MeOH was added 2.78 ml (5.56 mmol) of 2N NaOH followed by 0.33 ml (5.0 mmol) of 30% H2O. The reaction mixture was diluted with 10 ml of water and acidified with acetic acid. The mixture was extracted with EtOAc (3×20 ml). The combined organic phases were washed with brine and dried over MgSO4. The solution was filtered and the filtrate was concentrated in vacuo. The residue was recrystallized from MeOH to give 0.35 g of pale yellow needles. mp: 264°-266° C.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×20 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-d8a1e088e5da4de8bd11605b3d087e8f
Source dataset
uspto-grants-1994_07
Patent number
US05330987

Reaction notes

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