Reaction #465983

Reaction equation

Methyl 4-amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid

NaOH

→

white solid

Yield 56.5%

4-Amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic Acid

Yield 56.5%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated to dryness in vacuo and 100 mL each of diethyl ether and H2O
2. 2
   workup.ADDITIONadded
3. 3
   workup.ADDITIONMethylene chloride was added
4. 4
   Extractionthe aqueous phase was extracted with additional CH2Cl2 (2×100 mL)
5. 5
   DryingThe combined extracts were dried (MgSO4)
6. 6
   Concentrationconcentrated to dryness in vacuo

Procedure

To Methyl 4-amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid (0.0.720 g, 2.07 mmol) in 20 mL of methanol was added 1N NaOH (2.07 mL) and stirred at RT for 1 hr. The reaction mixture was concentrated to dryness in vacuo and 100 mL each of diethyl ether and H2O added. The aqueous layer acidified with 1N HCl until pH=2. Methylene chloride was added and the aqueous phase was extracted with additional CH2Cl2 (2×100 mL). The combined extracts were dried (MgSO4) and concentrated to dryness in vacuo to give 0.390 g of white solid 4-amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid (Compound 47); mp 196° C.

Source