Water → 4-(Hydroxymethyl)pyridine-2-carboxamide
Reaction equation
C[Si](Cl)(C)C.[C:6]([C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1)#[N:7].O.C(=O)([O-])[O-:18].[Na+].[Na+]>C(O)C>[C:6]([C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1)(=[O:18])[NH2:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Trimethylsilyl chloride (27 mL) and a suspension of 2-cyanopyridine-4-methanol (1.6 g, 11 mmol, Reference compound 11-1) in ethanol (20 mL) were added to ethanol (14 mL) at room temperature under a nitrogen atmosphere, and then the mixture was stirred at 50° C. for 5.5 hours. The mixture was allowed to stand, and water (27 mL) and sodium carbonate (2.3 g, 22 mmol) were added thereto. The solvent was evaporated under reduced pressure, ethanol (100 mL) was added thereto, and the resulting insoluble matter was filtered out. The filtrate was evaporated under reduced pressure, then the resulting residue was dried at 50° C. under reduced pressure to the title reference compound including inorganic salt.
Workup
- customThe solvent was evaporated under reduced pressure, ethanol (100 mL)
- additionwas added
- filtrationthe resulting insoluble matter was filtered out
- customThe filtrate was evaporated under reduced pressure
- customthe resulting residue was dried at 50° C. under reduced pressure to the title reference compound
Sources & evidence
- ORD record
- ord-6a566a1cbfcb4b14b46c0e50c7097f3e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518973B2
Reaction notes
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