Water → 3-(Cyclohexylmethoxy)-5-methyl-2-nitropyridine
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.Br[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[CH:14]1([CH2:13][O:11][C:4]2[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 78 °C
Procedure
A suspension of 1 g of 5-methyl-2-nitropyridin-3-ol, 1.35 ml of (bromomethyl)cyclohexane, and 1.79 g of potassium carbonate in 10 ml of DMF was stirred at 78° C. for 12 hours. After leaving to be cooled at room temperature, to the reaction mixture were added water and hexane/ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.8 g of 3-(cyclohexylmethoxy)-5-methyl-2-nitropyridine.
Workup
- customAfter leaving
- temperatureto be cooled at room temperature, to the reaction mixture
- customa layer separation operation
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a3c237c8dcc249478fb8b1f6f5f2c6ba
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447090B2
Reaction notes
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