Methanol → HCID 90417907, compound

HRID 633564Notes

Reaction equation

HRID 633564 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][N:9]([CH3:12])[C:5]2=[C:6](Cl)[N:7]=1.[CH3:13][O-:14].[Na+].CO>>[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][N:9]([CH3:12])[C:5]2=[C:6]([O:14][CH3:13])[N:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 90416413HCID 90416413, compound

Product 1

HCID 90417907HCID 90417907, compoundYield 97%

Conditions

Temperature
130 °C

Procedure

The product from Example 91A (0.43 g, 1.752 mmol) and 0.5 M sodium methoxide in methanol (15 mL, 7.50 mmol) were combined in a sealed microwave tube, heated by microwave at 130° C. for 45 minutes, cooled and concentrated. The residue was partitioned between ethyl acetate and water adjusting the pH to 7 with 1 M HCl. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated to afford the title compound (0.41 g, 97%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water adjusting the pH to 7 with 1 M HCl
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-251c2571eefc448bbffb8415d689fa1d
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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