1-Hydroxybenzotriazole → 2-Methylnicotinamide
Reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.C([N:14]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(C(=CC)C=CCN)C>ClCCl.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1[C:7]([C:8]([NH2:14])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-methyl-3-pyridinecarboxylic acid (1.66 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.12 g), and N-hydroxybenzotriazole (1.63 g) in dichloromethane (25 ml) was stirred at 0° C. for 15 minutes. A solution of 4-ethyl-2,4-hexadien-1-ylamine (1.26 g) in dichloromethane (6.3 ml) was added dropwise to the solution over a period of 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 3 hours. The reaction mixture was diluted with aqueous sodium hydrogen carbonate. The organic phase separated was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (4% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-2-methyl-3-pyridinecarboxamide 2.38 g) as an oil.
Workup
- waitat room temperature for 3 hours
- customThe organic phase separated
- washwas washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated in vacuo
- customThe residue was chromatographed on silica gel (4% methanol-chloroform)
Sources & evidence
- ORD record
- ord-fee2ad63d36546489dee71104eb1ddb5
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05495023
Reaction notes
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