Hydrogen Peroxide → 6-Chloro-5-methylnicotinic acid

HRID 2065881Notes

Reaction equation

HRID 2065881 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-methylnicotinic 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% wt 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 6-chloro-5-methyl-nicotinic acid (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-d11d72e279474c9cb5f9114e16d8b78d
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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