Sodium Hydroxide → 4-Amino-6-bromo-3-chloropicolinic acid

HRID 378777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378777
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11]C)=[O:10])[C:3]=1[Cl:13].[OH-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([OH:11])=[O:10])[C:3]=1[Cl:13]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22677536Methyl 4-amino-6-bromo-3-chloropicolinate

Produkt 1

HCID 216966234-Amino-6-bromo-3-chloropicolinic acidAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To methyl 4-amino-6-bromo-3-chloropyridine-2-carboxylate (200mg; 0.8 mmol) in 10 mL of methanol was added excess 2N NaOH (10 mL). The mixture was stirred for 1 hr at ambient temperature and then evaporated to dryness in vacuo. The residue was dissolved in water and diethyl ether. After separation of the phases, the aqueous layer was acidified with 1N HCl to a pH=2. The aqueous layer was evaporated to dryness and the residue was dissolved in 50 mL of methanol and filtered. The filtrate was evaporated under reduced pressure and the residue was triturated with 5 percent diethyl ether in petroleum ether to give 70 mg of 4-amino-6-bromo-3-chloropyridine-2-carboxylic acid, mp 182-183° C.

Aufarbeitung

  1. customevaporated to dryness in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customAfter separation of the phases
  4. customThe aqueous layer was evaporated to dryness
  5. dissolutionthe residue was dissolved in 50 mL of methanol
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was triturated with 5 percent diethyl ether in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6ac3d530c09e4333b5f41c578e14f103
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297197B1

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