Sodium Cyanide → HCID 57949779, compound

HRID 2427706Notes

Reaction equation

HRID 2427706 reaction equation
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=O)[NH:8][CH2:7]2.[C-]#[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>[CH2:9]([N:8]1[CH2:7][C:6]2[C:26](=[C:4]([C:5]#[N:13])[CH:3]=[CH:2][CH:10]=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 469118897-Iodo-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 57949779HCID 57949779, compoundYield 68%

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 7-iodo-2,3-dihydro-1H-isoindole-1-one (0.087 g, 0.25 mmol), Pd(PPh3)4 (0.031 g, 0.025 mmol), sodium cyanide (0.028 g, 0.6 mmol), and CuI (0.006 g, 0.025 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-7-carbonitrile (0.042 g, 68%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.32 (s, 2H), 4.82 (s, 2H), 7.33 (m, 5H), 7.61 (d, 2H), 7.78 (t, 1H).

Sources & evidence

ORD record
ord-54bdae2394b34459952c029a9d58b989
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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