Phthalimidine → 2-(1-Oxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile

HRID 2427572Notes

Reaction equation

HRID 2427572 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[O:10]=[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 579496372-(1-Oxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrileYield 44.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydro-isoindol-1-one (0.066 g, 0.5 mmol,), 2-bromomethyl-benzonitrile (0.117 g, 0.6 mmol), Cs2CO3 (0.408 g, 1.25 mmol), and 18-crown-6 (0.013 g, 0.05 mmol) in acetone (3 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile (0.055 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.22 (s, 2H), 5.08 (s, 2H), 7.28-7.70 (m, 7H), 7.92 (d, 1H).

Sources & evidence

ORD record
ord-ede20995f90c4ad390d82b15e5b568d8
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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