Reaction #465966

Reaction equation

3,6-dichloropyridine-2-carboxylic acid

methanol

→

light yellow solid

Methyl 3,6-Dichloropyridine-2-carboxylate

Conditions

Workup

1. 1
   OtherTo a 3-neck round bottom flask equipped with a reflux condenser
2. 2
   OtherHCl(g) was bubbled in until solution
3. 3
   ConcentrationThe solution was concentrated to dryness in vacuo
4. 4
   workup.ADDITIONDiethyl ether was added
5. 5
   workup.ADDITIONwas subsequently added to a flask
6. 6
   workup.ADDITIONfilled with a 1:1 mixture of saturated sodium bicarbonate/diethyl ether
7. 7
   workup.STIRRINGstirred for 10 min
8. 8
   ExtractionThe aqueous phase was extracted with diethyl ether (3×300 mL)
9. 9
   DryingThe combined extracts were dried (MgSO4)
10. 10
    Concentrationconcentrated

Procedure

To a 3-neck round bottom flask equipped with a reflux condenser was added 3,6-dichloropyridine-2-carboxylic acid (50.0 g, 260.42 mmol) in methanol (200 mL). HCl(g) was bubbled in until solution became saturated and stirred at room temperature for 2 hr. The solution was concentrated to dryness in vacuo. Diethyl ether was added to make a slurry that was subsequently added to a flask filled with a 1:1 mixture of saturated sodium bicarbonate/diethyl ether and stirred for 10 min. The aqueous phase was extracted with diethyl ether (3×300 mL). The combined extracts were dried (MgSO4) and concentrated to give 46.6 g of a light yellow solid. 1H NMR(CDCl3): δ 4.00 (s, 3H); 7.41 (d, 1H); 7.80 (d, 1H).

Source