Hydrochloric Acid → 4-Amino-3,5-dichloro-6-phenoxypyridine-2-carboxylic acid

HRID 378803Notes

Reaction equation

HRID 378803 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([C:16]([O:18]C)=[O:17])[C:3]=1[Cl:20].[OH-].[Na+].Cl>CO.O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([C:16]([OH:18])=[O:17])[C:3]=1[Cl:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21696627Methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate

Product 1

HCID 216966004-Amino-3,5-dichloro-6-phenoxypyridine-2-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate in methanol (10 mL) and water (100 mL) was added sodium hydroxide (0.5 g excess) and the solution heated under reflux for 3 hr. The solution was cooled and concentrated hydrochloric acid (2 mL) added. The solid was collected to give 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylic acid (1.1 g, 90%); mp 158-60° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 3 hr
  3. temperatureThe solution was cooled
  4. customThe solid was collected

Sources & evidence

ORD record
ord-1c5c1bf903f24451986300b2c11fb41a
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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