Water → HCID 68153594, compound

HRID 2204231Notes

Reaction equation

HRID 2204231 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[O:12][CH:13]([CH3:15])[CH3:14].[CH3:16][O-:17].[Na+].O>O1CCOCC1.Cl>[CH:13]([O:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[O:17][CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59504247HCID 59504247, compound

Product 1

HCID 68153594HCID 68153594, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 6-chloro-5-isopropoxypicolinate (330 mg, 1.437 mmol) was dissolved in dioxane (12 mL) before a solution of sodium methoxide (5.75 mL of 0.5 M in MeOH, 2.87 mmol) was added. The reaction was heated under microwave irradiation at 140° C. for 1.5 hours. Water (52 μL, 2.9 mmol) was added and the reaction mixture was heated by microwave irradiation at 100° C. for 30 minutes. The reaction mixture was diluted with 1 N HCl solution (50 mL) and was extracted with ethyl acetate (2×50 mL). Organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 5-isopropoxy-6-methoxypicolinic acid (300 mg, 98%) as a beige solid. 1H NMR (400 MHz, CDCl3) δ 7.83 (d, J=8.1 Hz, 1H), 7.17 (d, J=8.1 Hz, 1H), 4.72-4.61 (m, 1H), 4.06 (s, 3H), 1.45 (t, J=7.4 Hz, 6H). ESI-MS m/z calc. 211.1, found 211.9 (M+1)+; Retention time: 0.97 minutes (3 min run).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated by microwave irradiation at 100° C. for 30 minutes
  3. extractionwas extracted with ethyl acetate (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac655b20603a481aa6c2ab7bf5c03f95
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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