Potassium Hydroxide → HCID 67429636, compound

HRID 1661083Notes

Reaction equation

HRID 1661083 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12].Br[CH:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[C:7]2=[O:12]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 704604-BromoheptaneHCID 10061724HCID 10061724, compound

Product 1

HCID 67429636HCID 67429636, compoundYield 117.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

0.2 g of 5-iodo-2H-isoquinolin-1-one, 234 mg of 4-bromoheptane, 62 mg of finely ground potassium hydroxide, 79 mg of tetrabutylammonium bromide then 28 cm3 of toluene are stirred, under an inert atmosphere, for 6 h at the reflux of the solvent. The reaction mixture is filtered through sintered glass. The filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). The 320 mg of brown oil obtained are purified by flash chromatography over silica (column: 35 g; particle size: 20-40 μm, spherical; eluent: 80% heptane/20% ethyl acetate). After concentrating the fractions under reduced pressure, 165 mg of 5-iodo-2-(1-propylbutyl)isoquinolin-1(2H)-one are obtained in the form of a yellow solid.

Workup

  1. temperaturereflux of the solvent
  2. filtrationThe reaction mixture is filtered through sintered glass
  3. concentrationThe filtrate is concentrated
  4. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-eaafd86223054660b2789489ef94315e
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

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