Reaction #465980

Reaction equation

4-amino-6-trifluoromethylpyridine-2-carboxylic acid methyl ester

sulfuryl chloride

Et2O

→

product

Yield 24.5%

4-Amino-3-chloro-6-trifluoromethylpyridine-2-carboxylic Acid

Yield 24.5%

Solvents

CH3CN

CH3CN

Conditions

Workup

1. 1
   Otherreaction mixture
2. 2
   Washwashed with aqueous NaHCO3
3. 3
   Dryingdried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherto give a solid
7. 7
   OtherThe crude product was purified by chromatography
8. 8
   Washeluting with 10% ethyl acetate-hexane

Procedure

To a solution containing 4-amino-6-trifluoromethylpyridine-2-carboxylic acid methyl ester (0.75 g, 3.4 mmol) in 5 mL of CH3CN was added dropwise a solution of sulfuryl chloride (0.27 mL, 3.4 mmol) in 1 mL of CH3CN. After stirring at RT for 1 hr, reaction mixture was added to 50 mL of Et2O and washed with aqueous NaHCO3, dried over MgSO4, filtered and concentrated to give a solid. The crude product was purified by chromatography, eluting with 10% ethyl acetate-hexane to give 200 mg of product as a white solid; mp 131-3° C.

Source