Water → N-[3-(1-Hydroxyhexyl)phenyl]pyridine-2-carboxamide
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH2:18]([Mg]Br)[CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The aldehyde (1.1 g) was dissolved in dry tetrahydrofuran, and cooled in an ice bath. To this cold solution was added dropwise, a solution of pentylmagnesium bromide (prepared from 1-bromopentane (1.9 g) and magnesium turnings (0.31 g) in dry ether). The reaction mixture was stirred at 0° C. for two hours, allowed to warm to room temperature and was carefully poured into cold water. The aqueous solution was extracted with ethyl acetate, and the organic extract was washed with aqueous ammonium chloride solution, brine and then dried over anhydrous magnesium sulfate. All volatilss were removed to leave a viscous liquid which quickly solidified on standing. This solid was crystallized from ethyl acetate/hexane to give pure product.
Workup
- temperaturecooled in an ice bath
- additionTo this cold solution was added dropwise
- temperatureto warm to room temperature
- extractionThe aqueous solution was extracted with ethyl acetate
- extractionthe organic extract
- washwas washed with aqueous ammonium chloride solution, brine
- dry with materialdried over anhydrous magnesium sulfate
- customAll volatilss were removed
- customto leave a viscous liquid which
- customThis solid was crystallized from ethyl acetate/hexane
- customto give pure product
Sources & evidence
- ORD record
- ord-9abddd054c324cc0bb4643993a02d356
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04794188
Reaction notes
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