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

HRID 344887Notes

Reaction equation

HRID 344887 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 935NickelCatalyst2×HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

6,7,8-Trifluorocarbostyril (24.35 g), suspended in a mixture of ethanol (450 cc) and dimethylformamide (150 cc), is hydrogenated with stirring at approximately 50° C. in the presence of Raney nickel (5 g) under a pressure of 1 atmosphere, until the absorption of hydrogen is complete. The Raney nickel used, of W-2 grade, is washed beforehand with 2% aqueous acetic acid solution (50 cc), with water (2×50 cc) and with ethanol (3×50 cc). The reaction mixture is treated with dimethylformamide (250 cc) and filtered at approximately 50° C. through diatomaceous silica. The filtrate is concentrated under reduced pressure (20 kPa) at approximately 70° C. The dry extract is taken up with water (150 cc), drained and washed with water (2×50 cc). 6,7,8-Trifluoro-3,4-dihydrocarbostyril (23.6 g) is obtained in the form of a light beige solid, m.p. 217° C., which is used without further purification for the subsequent steps.

Workup

  1. washis washed
  2. additionThe reaction mixture is treated with dimethylformamide (250 cc)
  3. filtrationfiltered at approximately 50° C. through diatomaceous silica
  4. concentrationThe filtrate is concentrated under reduced pressure (20 kPa) at approximately 70° C
  5. extractionThe dry extract
  6. washwashed with water (2×50 cc)

Sources & evidence

ORD record
ord-e8494c25156d4036b87625243a3de648
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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