Potassium Carbonate → 1,6-Naphthyridin-2(1H)-One

HRID 979998Notes

Reaction equation

HRID 979998 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.FC(F)(F)C1N=CNC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:7]1[C:8]2[C:3](=[CH:2][N:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][C:6]1=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-oneHCID 178418921HCID 178418921, compound

Product 1

HCID 5896741,6-Naphthyridin-2(1H)-One

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a third run a mixture containing 3.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 8.5 g of 4-(trifluoromethyl)-1H-imidazole, 8.7 g of potassium carbonate and 150 ml of dimethylformamide was refluxed with stirring for 29 hours and following a work-up procedure as described in the preceding paragraphs, 1.9 g of the crude product was obtained. The three fractions of product were combined, recrystallized three times from isopropyl alcohol and dried in an oven at 100° C. for two days to yield 1.95 g of 5-[(4-trifluoromethyl)-1H-imidazol-1-yl)]-1,6-naphthyridin-2(1H)-one, m.p. 216°-218° C.

Workup

  1. temperaturewas refluxed
  2. custom1.9 g of the crude product was obtained
  3. customrecrystallized three times from isopropyl alcohol
  4. customdried in an oven at 100° C. for two days

Sources & evidence

ORD record
ord-596674f7608f4cb6921da4758adf66e6
Source dataset
uspto-grants-1987_01
Patent number
US04634772

Reaction notes

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