Sodium Carbonate → 5-bromo-2-(1-propylbutyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 387621Notes

Reaction equation

HRID 387621 reaction equation
C[O:2][C:3](=O)[N:4]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20])[CH:5]([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[Br:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH2:13][CH2:12][N:4]([CH:5]([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8])[C:3]2=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67749Trifluoromethanesulfonic anhydrideHCID 68474717Methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate

Product 1

HCID 684724385-bromo-2-(1-propylbutyl)-3,4-dihydroisoquinolin-1(2H)-oneYield 87.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

5.8 g of methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate are dissolved, under an inert atmosphere, in 250 cm3 of dichloromethane, at a temperature close to 20° C. 5.43 g of 4-dimethylaminopyridine are added to the reaction mixture. This is cooled to a temperature close to 0° C. 13 cm3 of trifluoromethanesulfonic anhydride in solution in 250 cm3 of anhydrous dichloromethane are poured into the reaction mixture over 45 min. The suspension is kept stirring for 20 h at a temperature close to 20° C. 300 cm3 of a saturated aqueous solution of sodium carbonate are added to the reaction mixture. The stirring is continued for 30 min. The organic phase is washed with 100 cm3 of a 20% aqueous solution of acetic acid, 100 cm3 of a saturated aqueous solution of sodium carbonate, and 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered through a pellet (50 g) of silica (particle size: 40-63 μm), rinsed with 500 cm3 of dichloromethane and concentrated using a rotary evaporator under reduced pressure (5 kPa). 4.63 g of 5-bromo-2-(1-propylbutyl)-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a yellow oil.

Workup

  1. customclose to 20° C
  2. temperatureThis is cooled to a temperature
  3. customclose to 0° C
  4. customclose to 20° C
  5. waitThe stirring is continued for 30 min
  6. washThe organic phase is washed with 100 cm3 of a 20% aqueous solution of acetic acid, 100 cm3 of a saturated aqueous solution of sodium carbonate, and 100 cm3 of a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered through a pellet (50 g) of silica (particle size: 40-63 μm)
  9. washrinsed with 500 cm3 of dichloromethane
  10. concentrationconcentrated
  11. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-9bbe7af680d64be5b57a57da980c39eb
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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