Isopropanol → 6-Methyl-5-nitropicolinic acid

HRID 2202380Notes

Reaction equation

HRID 2202380 reaction equation
[CH3:1][C:2]1[N:7]=C(C#N)[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C[C:14]([CH3:17])([O-:16])C.[K+].CC([OH:22])C>O>[CH3:1][C:2]1[N:7]=[C:17]([C:14]([OH:22])=[O:16])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 124040386-Methyl-5-nitropyridine-2-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 74720376-Methyl-5-nitropicolinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 6-methyl-5-nitropicolinonitrile (31B, 500 mg, 3.1 mmol) in 2-propanol (1 mL) and water (5 mL) was added potassium tert-butoxide (687 mg, 6.13 mmol). The mixture was stirred at 100° C. overnight, when LCMS indicated that the reaction was complete. The mixture diluted with water, and then extracted with DCM (10 mL×3). The aqueous phase was acidified with 1N HCl solution, and extracted with DCM. The organic layer was dried and concentrated to give the crude product which was used to the next step without further purification. LC-MS: m/z 181 (M−H)+

Workup

  1. extractionextracted with DCM (10 mL×3)
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8282117c87d4a7a94e71aace437da34
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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