Cyanoacetamide → 2-Methyl-4-methoxymethyl-5-cyano-6-oxypyridine
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
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
- additionwere added
- customreaction
- customOn completion, ethanol was evaporated
- additionwater was added to residue
- customSolid obtained
- filtrationwas filtered
- washwashed with water
- filtrationfiltered again
Sources & evidence
- ORD record
- ord-ff6f2837fbe2422793f2d1cc346c1b6e
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598167B1
Reaction notes
Loading…