Hydrochloric Acid → 4-Amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid

HRID 508541Notes

Reaction equation

HRID 508541 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([CH:19]=[O:20])[CH:3]=1.Cl([O-])=[O:22].[Na+].CC(=CC)C.P([O-])([O-])(O)=O.[Na+].[Na+].Cl>C(O)(C)(C)C.O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([OH:22])=[O:20])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 23668197Sodium ChloriteHCID 86723380HCID 86723380, compound

Product 1

HCID 867233814-Amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

In a typical reaction, 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinaldehyde is oxidized with an excess of sodium chlorite, between 20-30 equivalents of 2-methyl-2-butene and about 5 equivalents of disodium hydrogen phosphate in a t-butanol/water mixture. The mixture is heated at about 80° C. until the reaction is complete. After cooling, the mixture is treated with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer is separated and dried. The solvent is evaporated to provide crude 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinic acid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is separated
  4. customdried
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-06049c7b863b4c1f9ebd33cb986f1699
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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