Sodium Bicarbonate → HCID 11117620, compound

HRID 398831Notes

Reaction equation

HRID 398831 reaction equation
C([NH:7][C:8]1[C:13]([C:14](O)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15][C:16](OC(C)(C)C)=[O:17])=[CH:12][CH:11]=[CH:10][N:9]=1)(=O)C(C)(C)C.C(=O)(O)[O-].[Na+]>Cl.O1CCOCC1>[C:23]1([C:14]2[C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:16](=[O:17])[CH:15]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 10971347Tert-butyl 2-pivaloylamino-beta-hydroxy-beta-phenyl-3-pyridinepropanoate

Product 1

HCID 11117620HCID 11117620, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 2-pivaloylamino-β-hydroxy-β-phenyl-3-pyridinepropanoate (2.09 g, 5.25 mmol) was dissolved in a mixed solvent of 3N hydrochloric acid aqueous solution (10 ml) and dioxane (10 ml), and the solution was heated under reflux for 3 days. After cooling to room temperature, saturated sodium bicarbonate aqueous solution was added for neutralization. The reaction mixture was filtered, and the resulting crystals were thoroughly washed with water and recrystallized from acetonitrile to give 4-phenyl-1,8-naphthyridin-2(1H)-one (600 mg, 51%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 days
  3. filtrationThe reaction mixture was filtered
  4. washthe resulting crystals were thoroughly washed with water
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5401f47701eb412abe6a91350884ed53
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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