Water → HCID 58617236, compound

HRID 550359Notes

Reaction equation

HRID 550359 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([NH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]([O:22]CC)=O)=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[C:3]=1[CH:10]1[C:20](=[O:22])[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[NH:13][C:11]1=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 58617234HCID 58617234, compound

Product 1

HCID 58617236HCID 58617236, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Step 2 (3.0 g) and potassium carbonate (1.6 g) were stirred in dry DMF (100 ml) at 100° C. for 3 hours. The reaction was cooled and the excess DMF evaporated to give a black oil. Water (100 ml) was added and then washed with ethyl acetate. The aqueous fraction was filtered and acidified with 2M aqueous hydrochloric acid to neutral pH, and the water was evaporated to give a solid, which was then extracted with methanol. The methanol extract was evaporated to give the crude 3-(2,4,6-trifluorophenyl)-1H-[1,7]naphthyridine-2,4-dione as a dark brown crystalline solid (2.0 g), which was used for the next reaction without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. customthe excess DMF evaporated
  3. customto give a black oil
  4. washwashed with ethyl acetate
  5. filtrationThe aqueous fraction was filtered
  6. customthe water was evaporated
  7. customto give a solid, which
  8. extractionwas then extracted with methanol
  9. extractionThe methanol extract
  10. customwas evaporated

Sources & evidence

ORD record
ord-e1d4aee5544d403e8fd6b563f96e15d2
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Reaction notes

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