Nitromethane → 1-[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol
Reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[Na+].[N+:16]([CH3:19])([O-:18])=[O:17]>>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[CH2:19][N+:16]([O-:18])=[O:17])=[CH:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[N:9]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) (70 g, 1.0 eq.) in nitro methane (700 mL) was added sodium hydroxide (6.7 g, 0.5 eq.) at room temperature. The resulting reaction mixture was heated to 100° C. and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure to remove nitro methane quenched with ice water (500 mL) and extracted with ethyl acetate (2×1.0 L). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get pure 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (65.0 g, 72.0%).
Workup
- customThe resulting reaction mixture
- customAfter completion of reaction
- concentrationthe reaction mixture was concentrated under reduced pressure
- customto remove nitro methane
- customquenched with ice water (500 mL)
- extractionextracted with ethyl acetate (2×1.0 L)
- washThe combined organic layer was washed with water (500 mL), brine (500 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fd095199b01843ab9f17da757d74d52c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301526B2
Reaction notes
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