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

HRID 77390

Reaction equation

HRID 77390 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 184406222-Chloro-5-nitroisonicotinic acidYield 110.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4e907e611bb341da8e2279b2c1516cc7
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Linked notes

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