Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | 5-bromo-2,3-dihydro-1H-isoindol-1-one | HCID 22607119 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66873020 | HCID 66873020 | 85% |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968570B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-07c4577e46974969bb6dca9eb3baed9f |
|---|
| Source note | uspto-grants-2011_06 |
|---|
