Reaction #1833258

Reaction equation

sodium hydroxide

methyl 4-amino-6-(benzo[d][1,3]dioxol-4-yl)-3-chloro-5-fluoropicolinate

HCl

→

title compound

Yield 74.6%

4-Amino-6-(benzo[d][1,3]dioxol-4-yl)-3-chloro-5-fluoropicolinic acid

Yield 74.6%

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationconcentrated under a stream of nitrogen
2. 2
   OtherThe precipitate that formed
3. 3
   Filtrationwas filtered off
4. 4
   Washwashed with water
5. 5
   Otherdried

Procedure

To a reaction vessel containing methyl 4-amino-6-(benzo[d][1,3]dioxol-4-yl)-3-chloro-5-fluoropicolinate (0.150 g, 0.462 mmol) was added methanol (9.24 mL) and 2 N sodium hydroxide (0.924 mL, 1.848 mmol). The reaction mixture was stirred overnight at room temperature, neutralized to pH 3 with 2 N HCl, and concentrated under a stream of nitrogen. The precipitate that formed was filtered off, washed with water, and dried to provide the title compound as a white solid (0.107 g, 74.6%): mp 171-173° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.08-7.00 (m, 2H), 6.99-6.93 (m, 2H), 6.93 (br s, 2H), 6.06 (s, 2H); ESIMS m/z 311.2 ([M+H]+), 309.1 ([M−H]−).

Source