Water → HCID 68153594, compound

HRID 1405396Notes

Reaction equation

HRID 1405396 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.CO.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

7

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59504247HCID 59504247, compound

Product 1

HCID 68153594HCID 68153594, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 6-chloro-5-isopropoxy-pyridine-2-carboxylate (330 mg, 1.44 mmol) was dissolved in dioxane (12 mL), and a solution of sodium methoxide (5.75 mL of 0.5 M, 2.87 mmol) in methanol 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 extracted with EtOAc (2×50 mL). Organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 5-isopropoxy-6-methoxy-pyridine-2-carboxylic acid (300 mg, 98%) as a beige solid. ESI-MS m/z calc. 211.1, found 211.9 (M+1)+; Retention time: 0.97 minutes (3 min run). 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, 7H).

Workup

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

Sources & evidence

ORD record
ord-059a60154da74412ad4f4c3633ca5877
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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