Potassium Cyanide → 3-(Cyanomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin

HRID 17858Notes

Reaction equation

Br[CH2:2][C:3]1[N:4]([CH3:22])[C:5](=O)[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2.[C-:23]#[N:24].[K+]>C(O)(C)C.O>[C:23]([CH2:2][C:3]1[N:4]([CH3:22])[CH2:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2)#[N:24]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (6.82 g, 19.0 mmol) in 100 mL of isopropanol was added a solution of potassium cyanide (2.48 g, 38.1 mmol) in 10 mL of water. The mixture was heated at 80° C. After one hour, another portion of potassium cyanide solution (300 mg in 5 mL of water) was added, and the reaction stirred for an additional hour. The solution was cooled to room temperature, and partitioned between EtOAc and saturated NaHCO3 solution. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid material was triturated with EtOAc/ether to provide the titled product (5.01 g, 86% yield). HRMS (ES) exact mass calculated for C19H16N2O2 (M+H+): 305.1285. Found 305.1269.

Workup

temperatureThe solution was cooled to room temperature
custompartitioned between EtOAc and saturated NaHCO3 solution
extractionThe aqueous layer was extracted twice with EtOAc
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude solid material was triturated with EtOAc/ether

Sources & evidence

ORD record: ord-55c4291f19d9415dbe08cba8f6746645
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741322B2

Reaction notes

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