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

HRID 2065881

Reaktionsgleichung

Reaktionsgleichung von HRID 2065881
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d11d72e279474c9cb5f9114e16d8b78d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288554B2

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