Potassium Carbonate → HCID 64601728, compound

HRID 512042Notes

Reaction equation

HRID 512042 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([OH:17])=[O:16]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225994-(Bromomethyl)benzoic acidHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 64601728HCID 64601728, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 5-chloro-3-hydroxypyridine (0.6 g, 4.6 mmol) and potassium carbonate (1.27 g, 9.2 mmol) in acetone (10 mL) was added 4-carboxybenzylbromide (1.0 g, 4.6 mmol). The reaction was heated at reflux for 18 hours. After cooling, the reaction mixture was partitioned between EtOAc (80 mL) and saturated aqueous ammonium chloride solution (140 mL). The organic layer was dried over magnesium sulfate and evaporated in vacuo to afford the title compound (0.65 g, 53%), which was used in the next step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between EtOAc (80 mL) and saturated aqueous ammonium chloride solution (140 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-621e20abdf864dc6bbf7602e6a753e08
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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