Hydrogen Peroxide → 6-Chloro-5-methylpyridine-3-carboxylic acid

HRID 1908773

Reaction equation

HRID 1908773 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[CH3:10].[OH:11]O>C(O)=O.O>[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([C:8]([OH:11])=[O:9])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 197106816-Chloro-5-methylpyridine-3-carbaldehyde

Product 1

HCID 123877296-Chloro-5-methylpyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6-chloro-3-formyl-5-methyl-pyridine (10 g, 64 mmol) in formic acid (200 mL) is cooled at 0° C. and an aq. 50% weight solution of H2O2 in water (9.6 mL, 360 mmol) is added at this temperature. The mixture is stirred at 0° C. for 15 h, carefully diluted with water (200 mL) and extracted with DCM (8×100 mL). The combined org. extracts are washed with 1M aq. HCl (100 mL) (check for remaining peroxide), dried (MgSO4), filtered and evaporated. The residue is dried to give the title compound (9.56 g); LC-MS: tR=0.72 min, [M+1]+=172.0.

Workup

  1. extractionextracted with DCM (8×100 mL)
  2. washextracts are washed with 1M aq. HCl (100 mL) (check for remaining peroxide)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is dried

Sources & evidence

ORD record
ord-7686e5af131c4baf98a80d74894b3898
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Linked notes

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