Cyanoacetamide → 2-Methyl-4-methoxymethyl-5-cyano-6-oxypyridine

HRID 42480

Reaction equation

HRID 42480 reaction equation
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6](=O)[CH3:7].[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].N1CCCCC1>CCO.O>[CH3:7][C:6]1[NH:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=1

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 2217341-Methoxy-2,4-pentanedione

Product 1

HCID 949992-Methyl-4-methoxymethyl-5-cyano-6-oxypyridineYield 65.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

1-(Methyloxy)-2,4-pentanedione (9.51 g, 73.12 mmol) and cyanoacetamide (6.17 g, 73.12 mmol) were dissolved in EtOH (76 mL) and heated until homogenous (ca. 75° C.). Piperidine (6.25 g, 73.12 mmol) was added and the reaction mixture heated at reflux for 20 mins, followed by cooling to room temperature. The contents were filtered to give a solid which was suspended in 140 mL water and stirred vigorously for 20 min. The heterogenous mixture was filtered to afford 6-methyl-4-[(methyloxy)methyl]-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (7.8 g, 65.6%). LCMS MH+=179.0 1H NMR (400 MHz, DMSO-d6) δ 12.47 (br s, 1H), 6.26 (s, 1H), 4.40 (s, 2H), 3.29 (s, 3H), 2.25 (s, 3H).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 20 mins
  3. temperatureby cooling to room temperature
  4. filtrationThe contents were filtered
  5. customto give a solid which
  6. filtrationThe heterogenous mixture was filtered

Sources & evidence

ORD record
ord-fc44731c424045ea96cf333f2a7f002d
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Linked notes

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