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

HRID 1501616Notes

Reaction equation

HRID 1501616 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6](=O)[CH3:7].[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].C(O)(=O)C.N1CCCCC1.N1CCCCC1>C(O)C.O.C(O)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH3:7])[NH:14][C:12](=[O:13])[C:11]=1[C:9]#[N:10]

Participants

8

Reactant 4

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 833033-Pentyn-2-one, 5-methoxy-HCID 9793820Piperidine, acetate

Product 1

HCID 949992-Methyl-4-methoxymethyl-5-cyano-6-oxypyridineYield 8.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-methoxypent-3-yn-2-one (1.2 g, 10.7 mmol) in 90% ethanol (22 mL), cyanoacetamide (1.08 g, 12.85 mmol) and piperidine acetate {prepared by the addition of piperidine to a solution of acetic acid (0.5 mL) in water (1 mL) till pH 8} were added and reaction heated at 90° C. for 16 h. On completion, ethanol was evaporated and water was added to residue. Solid obtained was filtered and washed with water. Then this solid was stirred with acetonitrile for 10 min and filtered again to obtain the desired intermediate (0.165 g, 8.68%).

Workup

  1. additionwere added
  2. customreaction
  3. customOn completion, ethanol was evaporated
  4. additionwater was added to residue
  5. customSolid obtained
  6. filtrationwas filtered
  7. washwashed with water
  8. filtrationfiltered again

Sources & evidence

ORD record
ord-8e2dae3e1f4e4400944e86fb2fc11b9f
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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