Sodium Bicarbonate → HCID 178522255, compound

HRID 1179679Notes

Reaction equation

HRID 1179679 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.Cl.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[N:17][CH:18]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][C:13]2[CH:18]=[N:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27821656-Chloronicotinoyl ChlorideHCID 178479090HCID 178479090, compound

Product 1

HCID 178522255HCID 178522255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-nicotinoyl chloride (0.40 g, 2.27 mmol) and 5-amino-2-hydroxypyridine hydrochloride (0.33 g, 2.25 mmol) in dry tetrahydrofuran (15 mL) was stirred at room temperature for 1 hour. Saturated sodium bicarbonate (aq) was added and the solution was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was dissolved in a mixture of methanol (10 mL) and aqueous sodium hydroxide (1N, 2 mL). After stirring for 2 hours at room temperature water was added and the solution was extracted with dichloromethane. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo, yielding the title compound which was used without further purification.

Workup

  1. extractionthe solution was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in a mixture of methanol (10 mL) and aqueous sodium hydroxide (1N, 2 mL)
  6. additionwas added
  7. extractionthe solution was extracted with dichloromethane
  8. dry with materialThe organic layer was dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-dc6c33c39e0547579332bfd09f771121
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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