Reaction #465965

Reaction equation

sodium bicarbonate

methyl 3,6-dichloro-5-methoxy-4-nitropyridine-2-carboxylate

SnCl2

→

yellow solid

Yield 93.9%

Methyl 4-Amino-3,6-dichloro-5-methoxypyridine-2-carboxylate

Yield 93.9%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   ExtractionThe mixture was extracted with ethyl acetate
3. 3
   Otherthe layers were separated
4. 4
   WashThe aqueous layer was washed 2 more times with ethyl acetate
5. 5
   DryingThe combined organic layers were dried (MgSO4)
6. 6
   Concentrationconcentrated to dryness

Procedure

To methyl 3,6-dichloro-5-methoxy-4-nitropyridine-2-carboxylate (0.300 g, 1.06 mmol) in 5 mL of ethyl acetate was added SnCl2×2H2O (1.60 g, 7.1 mmol). The reaction mixture was heated to 70° C. for 30 min and then cooled to room temperature. Saturated sodium bicarbonate and a saturated solution of KHF2 were added to reaction mixture. The mixture was extracted with ethyl acetate and the layers were separated. The aqueous layer was washed 2 more times with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated to dryness to give 0.250 g of a yellow solid.

Source