Reaction #465973

Reaction equation

methyl 4-amino-6-bromo-3-methoxypyridine-2-carboxylate

NaOH

→

light pink solid

Yield 63.4%

4-Amino-6-bromo-3-methoxypyridine-2-carboxylic Acid

Yield 63.4%

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationconcentrated to dryness in vacuo
2. 2
   workup.ADDITIONDiethyl ether and H2O were added
3. 3
   Concentrationconcentrated to dryness
4. 4
   workup.ADDITIONMethanol (50 mL) was added to the white solid
5. 5
   FiltrationThe mixture was filtered
6. 6
   Concentrationthe filtrate concentrated to dryness
7. 7
   OtherTriturating with 5% diethyl ether/pet ether

Procedure

To methyl 4-amino-6-bromo-3-methoxypyridine-2-carboxylate (0.300 g, 1.15 mmol) in 10 mL of methanol was added 1N NaOH (1.15 mL, 1.15 mmol). The reaction mixture was stirred at room temperature for 1 hr and concentrated to dryness in vacuo. Diethyl ether and H2O were added. The aqueous layer was acidified with 1N HCl until pH=2 and concentrated to dryness. Methanol (50 mL) was added to the white solid. The mixture was filtered and the filtrate concentrated to dryness. Triturating with 5% diethyl ether/pet ether gave 0.180 g of a light pink solid. 1H NMR(DMSO): δ 3.60 (s, 3H); 6.80 (S, 1H).

Source