Potassium Hydroxide → HCID 86709870, compound

HRID 2206981Notes

Reaction equation

HRID 2206981 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([O:19]C(C)C)=[O:18])[CH:3]=1.[OH-].[K+]>O1CCCC1.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[N:5]=[C:4]([C:17]([OH:19])=[O:18])[CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86709871HCID 86709871, compound

Product 1

HCID 86709870HCID 86709870, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of isopropyl 4,5-dichloro-6-(4-methoxyphenyl)picolinate (5.25 g, 15.4 mmol) in tetrahydrofuran (40 mL) and water (10 mL) was added potassium hydroxide (1.26 g, 22.4 mmol). The reaction was allowed to stir at room temperature for 12 h. After 1 hour of stirring, solids precipitated from the mixture. HCl (aq) (2N, 25 mL) was added to the reaction mixture to form a clear biphasic mixture. The mixture was added to water (75 mL) in a reparatory funnel and extracted with EtOAc (2×75 mL). The combined organic layers were washed with water (25 mL) and saturated NaCl (50 mL) and then concentrated under reduced pressure to provide 4.57 g (99% yield) of 4,5-dichloro-6-(4-methoxyphenyl)picolinic acid as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.72-7.64 (m, 2H), 7.07-6.99 (m, 2H), 3.89 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 162.78, 161.05, 157.26, 146.30, 143.76, 133.54, 130.98, 128.72, 123.45, 113.77, 55.48.; mp=164-181° C.

Workup

  1. stirringAfter 1 hour of stirring
  2. customsolids precipitated from the mixture
  3. additionHCl (aq) (2N, 25 mL) was added to the reaction mixture
  4. customto form a clear biphasic mixture
  5. extractionextracted with EtOAc (2×75 mL)
  6. washThe combined organic layers were washed with water (25 mL) and saturated NaCl (50 mL)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3ef65df15574092be2d06fd3cdf2e70
Source dataset
uspto-grants-2016_06
Patent number
US09376388B2

Reaction notes

Loading…