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

HRID 1073602Notes

Reaction equation

HRID 1073602 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
  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-00dab238f3a8425a962710c0fbb126ad
Source dataset
uspto-grants-1990_11
Patent number
US04970213

Reaction notes

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