2,6-Dichloro-4-methylnicotinamide → 2,6-Dichloro-4-methylpyridine-3-carboxylic acid

HRID 1696917Notes

Reaction equation

HRID 1696917 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4](N)=[O:5].C(OC(=O)C)(=[O:15])C.C(O)(=O)C.N([O-])=O.[Na+]>C(OCC)C>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:15])=[O:5]

Participants

5

Reactant 3

HCID 3348552,6-Dichloro-4-methylnicotinamideHCID 21895370AcOH AcOAcHCID 23668193Sodium Nitrite

Product 1

HCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,6-dichloro-4-methyl-nicotinamide (6.40 g) in 2:1 acetic anhydride/acetic acid (156 mL) was treated with sodium nitrite (21.5 g), stirred for 18 hours, poured into diethyl ether (600 mL) and filtered. The filtrate was concentrated with a toluene azeotrope, and the concentrate was treated with brine and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated; and this concentrate was suspended in hexane, sonicated and filtered.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated with a toluene azeotrope
  3. additionthe concentrate was treated with brine
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customsonicated
  9. filtrationfiltered

Sources & evidence

ORD record
ord-28d034e028404a93aa6c8f12b959d2cd
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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