Reaction #710500

Reaction equation

2-chloro-6-(trifluoromethyl)nicotinaldehyde

sodium hydroxide

nitro methane

→

1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

Yield 72.0%

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   OtherAfter completion of reaction
3. 3
   Concentrationthe reaction mixture was concentrated under reduced pressure
4. 4
   Otherto remove nitro methane
5. 5
   Otherquenched with ice water (500 mL)
6. 6
   Extractionextracted with ethyl acetate (2×1.0 L)
7. 7
   WashThe combined organic layer was washed with water (500 mL), brine (500 mL)
8. 8
   Dryingdried over anhydrous sodium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

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%).

Source