Tetrahydrofuran → HCID 18969213, compound

HRID 398832Notes

Reaction equation

HRID 398832 reaction equation
CC(C)([O-])C.[K+].O1CCCC1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[C:16]([C:18]1[C:19]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])=[N:20][CH:21]=[CH:22][CH:23]=1)=O>O>[Cl:12][C:13]1[CH:14]=[C:15]([C:16]2[C:18]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:24]([CH3:28])[C:25](=[O:27])[CH:26]=2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18969175HCID 18969175, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969213HCID 18969213, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, potassium tert-butoxide (623 mg, 5 mmol) was added to tetrahydrofuran (10 ml) solution of N-[3-(3-chlorobenzoyl)-2-pyridyl]-N-methylacetamide (1.40 g, 5 mmol), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was mixed with water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (benzene-ethyl acetate) to give 4-(3-chlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one (709 mg, 54%).

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (benzene-ethyl acetate)

Sources & evidence

ORD record
ord-923074a2499a49528e218bd2590d53d3
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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