Sodium Cyanide → HCID 66873020, compound

HRID 2427705Notes

Reaction equation

HRID 2427705 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)C(=O)[NH:6][CH2:5]2.[C-:12]#[N:13].[Na+].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CCO[C:24]([CH3:26])=[O:25]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:12]([N:13]1[CH2:10][C:2]2[C:26](=[CH:9][CH:8]=[C:4]([C:5]#[N:6])[CH:3]=2)[C:24]1=[O:25])[C:17]1[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 21226206Ethyl acetate hexaneHCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 66873020HCID 66873020, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2,3-dihydro-1H-isoindole-1-one (0.065 g, 0.22 mmol), Pd(PPh3)4 (0.025 g, 0.02 mmol), sodium cyanide (0.023 g, 0.5 mmol), and CuI (0.004 g, 0.02 mmol) in acetonitrile (4 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate (typically 2:1 hexane-EtOAc) afforded 2-benzyl-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile (0.047 g, 85%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.32 (s, 2H), 4.81 (s, 2H), 7.33 (m, 5H), 7.68 (s, 1H), 7.76 (d, 1H), 7.98 (d, 1H). GC-MS: m/z 248 (M)+, 171 (M−77)+.

Sources & evidence

ORD record
ord-07c4577e46974969bb6dca9eb3baed9f
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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