Acetic Acid → 6-Isopropyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 607189Notes

Reaction equation

HRID 607189 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[C:7](O)(=O)C.N1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O)(=O)C>O>[CH:13]([C:14]1[NH:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[CH:16][CH:15]=1)([CH3:7])[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 9793820Piperidine, acetate

Product 1

HCID 105831136-Isopropyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the product of Example 36A (5.35 g, 0.0393 mol) and 2-cyanoacetamide (3.47 g, 0.0413 mol) in water (35 mL) was stirred at room temperature for 10 minutes. To this mixture was added 2.5 mL of a stock piperidine acetate solution (prepared from 9.8 mL of piperidine, 6 mL of acetic acid and 10 mL of water), and the solution was heated under reflux for 2 hours. The mixture was then cooled to room temperature and taken to pH 4 by the addition of glacial acetic acid. The resulting light yellow solid was isolated by vacuum filtration, rinsed with water (2×30 mL), and dried under vacuum to provide the title product (4.36 g, 68%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customThe resulting light yellow solid was isolated by vacuum filtration
  4. washrinsed with water (2×30 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cd53476804fb4b6bb53ce62ddaafd694
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…