Methyl 2-(cyanomethyl)-3-fluorobenzoate → 5-Fluoro-3,4-dihydroisoquinolin-1(2H)-one

HRID 2301128Notes

Reaction equation

HRID 2301128 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][C:12]#[N:13]>[Ni].C(O)C>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[CH2:11][CH2:12][NH:13][C:3]2=[O:2]

Participants

4

Reactant 1

HCID 54538594Methyl 2-(cyanomethyl)-3-fluorobenzoate

Product 1

HCID 183772915-Fluoro-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Ethanol and Raney nickel (Aldrich) were added to 2-cyanomethyl-3-fluoro-benzoic acid methyl ester (3.3 g, 17 mmol) to carry out catalytic reduction under ordinary pressure at 50° C. for 7 hours and then at room temperature for 15 hours. Raney nickel was removed from the reaction solution by filtration, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 2.1 g (13 mmol, 74% in yield) of the title compound.

Workup

  1. customat 50° C.
  2. customfor 7 hours
  3. customRaney nickel was removed from the reaction solution by filtration
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe thus obtained material was separated
  6. custompurified by a silica gel column chromatography
  7. customto obtain

Sources & evidence

ORD record
ord-fb55b803bf6e40ae929447aeab59000b
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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