Sodium dichromate dihydrate → 2-Chloro-5-nitroisonicotinic acid

HRID 77390

Reaktionsgleichung

Reaktionsgleichung von HRID 77390
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[OH2:12].[OH2:13].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1)[C:8]([OH:13])=[O:12]

Komponenten

4

Edukt 2

HCID 108005Sodium dichromate dihydrateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Produkt 1

HCID 184406222-Chloro-5-nitroisonicotinic acidAusbeute 110,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

2-chloro-4-methyl-5-nitropyridine (1.0 g, 5.8 mmol) was cooled using an ice water bath. Sodium dichromate dihydrate (3.45 g, 11.6 mmol) dissolved in sulphuric acid (50 mL) was added dropwise, ensuring reaction temperature does not exceed 15° C. After complete addition, reaction allowed to warm to room temperature and stirred overnight. Quenched with ice, extracted into ethylacetate and concentrated under reduced pressure to afford 2-chloro-5-nitroisonicotinic acid (1.3 g, 6.4 mmol).

Aufarbeitung

  1. additionwas added dropwise
  2. customreaction temperature
  3. customdoes not exceed 15° C
  4. additionAfter complete addition, reaction
  5. customQuenched with ice
  6. extractionextracted into ethylacetate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4e907e611bb341da8e2279b2c1516cc7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841289B2

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