Isopropanol → HCID 86709872, compound

HRID 541049Notes

Reaction equation

HRID 541049 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]([O:18]C(C)C)=[O:17])[CH:3]=1.C(O)(C)C.[OH-].[K+]>O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]([OH:18])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 86709873HCID 86709873, compound

Product 1

HCID 86709872HCID 86709872, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a 125 mL 3-neck round bottom flask fitted with a condenser, nitrogen inlet, overhead stirrer, thermometer and heating mantle was charged isopropyl 4,5-dichloro-6-(4-chlorophenyl)picolinate (7.6 g, 22.1 mmol) and isopropyl alcohol (70 mL). Reaction mixture was heated to 40° C. and potassium hydroxide (85%, 5.1 g, 77.4 mmol) and water (5 mL) were added. Solids precipitated from the mixture, and it became difficult to stir. The mixture was diluted with water (250 mL) to dissolve most of the solids and allowed to stir at room temperature. Concentrated HCl (12 N, 5.6 mL) was added dropwise to the reaction mixture to achieve a pH of ˜2 and solids precipitated from the mixture. The solids were isolated by vacuum filtration and washed with water (2×100 mL), then allowed to dry to give 7.3 g (108% yield by weight) of 4,5-dichloro-6-(4-chlorophenyl)picolinic acid as a white solid. 1H NMR (400 MHz, THF-d8/D2O) δ 8.19 (d, J=11.2 Hz, 1H), 7.84-7.73 (m, 2H), 7.50 (dd, J=10.3, 3.5 Hz, 2H); 13C NMR (101 MHz, THF-d8/D2O) δ 167.70, 156.03, 152.40, 143.60, 136.49, 134.76, 131.22, 129.24, 128.04, 124.71; mp=229° C.

Workup

  1. customTo a 125 mL 3-neck round bottom flask fitted with a condenser, nitrogen inlet
  2. temperatureoverhead stirrer, thermometer and heating mantle
  3. customReaction mixture
  4. customSolids precipitated from the mixture, and it
  5. additionThe mixture was diluted with water (250 mL)
  6. dissolutionto dissolve most of the solids
  7. stirringto stir at room temperature
  8. additionConcentrated HCl (12 N, 5.6 mL) was added dropwise to the reaction mixture
  9. customprecipitated from the mixture
  10. customThe solids were isolated by vacuum filtration
  11. washwashed with water (2×100 mL)
  12. customto dry

Sources & evidence

ORD record
ord-ea376bdafcd8470885a511a50848f19f
Source dataset
uspto-grants-2014_10
Patent number
US08871943B2

Reaction notes

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