Methanol → HCID 58318886, compound

HRID 2401499Notes

Reaction equation

HRID 2401499 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[CH3:20]O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:12]2[CH:17]=[N:16][CH:15]=[N:14][CH:13]=2)[CH:10]=1)[C:5]([O:7][CH3:20])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67051407HCID 67051407, compound

Product 1

HCID 58318886HCID 58318886, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

3-Chloro-5-(pyrimidin-5-yloxy)benzoic acid (464 mg, 1.85 mmol, 1 eq) was dissolved in methanol (9.3 mL) in a microwave vial and H2SO4 (0.93 mL) was added dropwise. The vial was capped and heated at 75° C. for 3 h. The reaction was cooled to rt and neutralized with 1N NaOH. The reaction was extracted with EtOAc (2×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 414 mg (84%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 8.74 (s, 2H), 7.75 (t, J=1.7 Hz, 1H), 7.65 (t, J=2.2 Hz, 1H), 7.54 (dd, J=1.4, 1.0 Hz, 1H), 3.84 (s, 3H); [M+1]+: 265.1.

Workup

  1. additionwas added dropwise
  2. customThe vial was capped
  3. extractionThe reaction was extracted with EtOAc (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d6bb697519b144c2bd8457abb795ff64
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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