Hydrochloric Acid → Indolauxipyr

HRID 923698Notes

Reaction equation

HRID 923698 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]([F:18])=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21]C)=[O:20])[C:3]=1[Cl:23].[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]([F:18])=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([OH:21])=[O:20])[C:3]=1[Cl:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 78319091methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate

Product 1

HCID 90417980IndolauxipyrYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a reaction vessel containing methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate (0.500 g, 1.481 mmol) was added methanol (14.81 ml) and sodium hydroxide (2.96 ml, 5.92 mmol). The reaction mixture was stirred overnight at rt then acidfied by adding a slight excess of 2N HCl. The mixture was concentrated and the precipitate that formed was washed with water and dried under vacuum to provide 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (0.400 g, 1.174 mmol, 79% yield) as an off-white solid:

Workup

  1. concentrationThe mixture was concentrated
  2. customthe precipitate that formed
  3. washwas washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6b145790cd784d239851521f3c168ad2
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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