Methanol → Clopyralid-methyl

HRID 378784Notes

Reaction equation

HRID 378784 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH3:12]O>>[Cl:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 15553Clopyralid

Product 1

HCID 526485Clopyralid-methyl

Procedure

To a 3-neck round bottom flask equipped with a reflux condenser was added 3,6-dichloropyridine-2-carboxylic acid (50.0 g, 260.42 mmol) in methanol (200 mL). HCl(g) was bubbled in until solution became saturated and stirred at room temperature for 2 hr. The solution was concentrated to dryness in vacuo. Diethyl ether was added to make a slurry that was subsequently added to a flask filled with a 1:1 mixture of saturated sodium bicarbonate/diethyl ether and stirred for 10 min. The aqueous phase was extracted with diethyl ether (3×300 mL). The combined extracts were dried (MgSO4) and concentrated to give 46.6 g of a light yellow solid. 1H NMR(CDCl3): δ 4.00 (s, 3H); 7.41 (d, 1H); 7.80 (d, 1H).

Workup

  1. customTo a 3-neck round bottom flask equipped with a reflux condenser
  2. customHCl(g) was bubbled in until solution
  3. concentrationThe solution was concentrated to dryness in vacuo
  4. additionDiethyl ether was added
  5. additionwas subsequently added to a flask
  6. additionfilled with a 1:1 mixture of saturated sodium bicarbonate/diethyl ether
  7. stirringstirred for 10 min
  8. extractionThe aqueous phase was extracted with diethyl ether (3×300 mL)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-964e8f1c76be44a193d614288924623d
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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