Water → 5-Bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one

HRID 387659Notes

Reaction equation

HRID 387659 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12].[H-].[Na+].Br[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:17].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:17])[C:7]2=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 133890301-(1-Bromoethyl)-4-fluorobenzeneHCID 218654725-Bromo-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 684736405-Bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-oneYield 140.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.15 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one in 5 cm3 of dimethylformamide is poured into a mixture containing 31 mg of sodium hydride (60% in oil) and 10 cm3 of dimethylformamide at a temperature close to 20° C. under an inert atmosphere. Then a solution of 0.2 g of 1-(1-bromoethyl)-4-fluorobenzene in 5 cm3 of dimethylformamide is poured into the reaction mixture. The latter is stirred for 20 h at a temperature close to 20° C. Water and ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 325 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 20% ethyl acetate/80% cyclohexane). After concentrating the fractions under reduced pressure, 146 mg of 5-bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a thick pale yellow oil.

Workup

  1. customclose to 20° C. under an inert atmosphere
  2. customclose to 20° C
  3. customAfter decanting
  4. washthe organic phase is washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthen concentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-dc5b1c0e40c541f4a6f28edc1840f99e
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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