6,7,8-Trifluorocarbostyril → 6,7,8-Trifluoro-3,4-dihydrocarbostyril

HRID 1084396Notes

Reaction equation

HRID 1084396 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[F:12])[NH:8][C:7](=[O:14])[CH:6]=[CH:5]2.[H][H]>C(O)C.CN(C)C=O.[Ni]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[F:12])[NH:8][C:7](=[O:14])[CH2:6][CH2:5]2

Participants

6

Reactant 2

HCID 199348726,7,8-TrifluorocarbostyrilHCID 178418361HCID 178418361, compound

Product 1

HCID 542457346,7,8-Trifluoro-3,4-dihydrocarbostyrilYield 95.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

24.35 g of 6,7,8-trifluorocarbostyril in suspension in a mixture of 450 cm3 of ethanol and 150 cm3 of dimethylformamide are hydrogenated, with stirring, at about 50° C., in the presence of 5 g of Raney nickel under a pressure of 1 atmosphere until the absorption of hydrogen has ceased. The W-2 grade Raney nickel used is washed beforehand with 50 cm3 of an aqueous 2% acetic acid solution, twice 50 cm3 of water and 3 times 50 cm3 of ethanol. 250 cm3 of dimethylformamide are added to the reaction mixture and the mixture is filtered at about 50° C. through diatomaceous silica. The filtrate is concentrated under reduced pressure (20 kPa) at about 70° C. The dry extract is taken up in 150 cm3 of water, drained and washed with twice 50 cm3 of water. 23.6 g of 6,7,8-trifluoro-3,4-dihydrocarbostyril are obtained in the form of a light beige solid melting at 217° C., which is used for the subsequent steps without further purification.

Workup

  1. washThe W-2 grade Raney nickel used is washed
  2. addition250 cm3 of dimethylformamide are added to the reaction mixture
  3. filtrationthe mixture is filtered at about 50° C. through diatomaceous silica
  4. concentrationThe filtrate is concentrated under reduced pressure (20 kPa) at about 70° C
  5. extractionThe dry extract
  6. washwashed with twice 50 cm3 of water

Sources & evidence

ORD record
ord-d7c17eeed0e9422685ebcb71f5a7cdf7
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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