Cyanoacetamide → 5-Fluoro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1959312Notes

Reaction equation

HRID 1959312 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[F:7][CH:8]([C:12](=O)[CH3:13])[C:9](=O)[CH3:10].N1CCCCC1>CCO>[F:7][C:8]1[C:12]([CH3:13])=[C:3]([C:1]#[N:2])[C:4](=[O:5])[NH:6][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 116266523-Fluoropentane-2,4-dione

Product 1

HCID 671241755-Fluoro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-cyanoacetamide (689 mg, 8.2 mmol) in anhydrous EtOH (7.0 ml) at 75° C., was added 3-fluoropentane-2,4-dione (880 mg, 7.5 mmol), followed by piperidine (96 μl, 0.97 mmol). The reaction mixture was stirred at this temperature for 3 hours and the reaction mixture left to reach room temperature before being stored in the refrigerator for 4 days. The beige solid was collected by filtration and rinsed with cold EtOH (4×0.4 ml) until the filtrate ran clear. The resulting beige solid was dried in-vacuo at 40° C. for 5 hours to give the title compound (733 mg, 58%) as a beige solid. LC-MS 97%, 1.18 min (3.5 minute LC-MS method); m/z=166.9, 1H NMR (500 MHz, Chloroform-d) δ ppm 13.67 (br. s., 1H) 2.46 (d, J=2.05 Hz, 3H) 2.45 (d, J=2.84 Hz, 3H).

Workup

  1. waitthe reaction mixture left
  2. customto reach room temperature
  3. waitbefore being stored in the refrigerator for 4 days
  4. filtrationThe beige solid was collected by filtration
  5. washrinsed with cold EtOH (4×0.4 ml) until the filtrate
  6. customThe resulting beige solid was dried in-vacuo at 40° C. for 5 hours

Sources & evidence

ORD record
ord-2bb253f962134bf7a955affbc4ff1afc
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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