Toluene → Methyl 2,6-dichloroisonicotinate

HRID 2233823Notes

Reaction equation

HRID 2233823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[C:16]1(C)C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 93237Methyl 2,6-dichloroisonicotinate

Procedure

2,6-Dichloroisonicotinic acid was (5 g, 26.04 mmol) was suspended in anhydrous toluene (75 ml). Thionyl chloride (19 ml, 260.4 mmol) was added and the mixture was heated to reflux for 4 h. The excess thionyl chloride was removed and solvent was removed in vacuo. Anhydrous MeOH (25 ml) was added and reaction was stirred for a further 4 h. Solvents were removed in vacuo to give a white colored solid which was dried under vacuum (4.8 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe excess thionyl chloride was removed
  4. customsolvent was removed in vacuo
  5. additionAnhydrous MeOH (25 ml) was added
  6. customreaction
  7. customSolvents were removed in vacuo
  8. customto give a white colored solid which
  9. customwas dried under vacuum (4.8 g)

Sources & evidence

ORD record
ord-59571bdfeca54eae9e5631e3ea776d29
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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