Sodium Methoxide → HCID 90102796, compound

HRID 1052637Notes

Reaction equation

HRID 1052637 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:5](Cl)=[N:6][CH:7]=1.[CH3:19][O-:20].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:5]([O:20][CH3:19])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 90103002HCID 90103002, compound

Product 1

HCID 90102796HCID 90102796, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzamide (600 mg, 1.83 mmol) was suspended in a solution of sodium methoxide 25% in methanol (12 ml, 55 mmol and the reaction mixture was stirred at 50° C. overnight. The solvent was removed and the crude poured into water. The precipitate was filtered off and discarded and the filtrate was brought to pH7 by adding hydrogen chloride 2N. The precipitate was then filtered and washed with water and was purified using SP1® Purification System (0% to 25%, hexane-ethyl acetate) to give 74 mg (8% yield) of the title compound. Purity 62%.

Workup

  1. customThe solvent was removed
  2. additionthe crude poured into water
  3. filtrationThe precipitate was filtered off
  4. additionby adding hydrogen chloride 2N
  5. filtrationThe precipitate was then filtered
  6. washwashed with water
  7. customwas purified
  8. customSP1® Purification System (0% to 25%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7a5c7a8aafd14b36aae75c67d8b4772c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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