Phthalimidine → HCID 57295525, compound

HRID 2427573Notes

Reaction equation

HRID 2427573 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:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19].C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10]

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 2855718-Crown-6

Product 1

HCID 57295525HCID 57295525, compoundYield 27.2%

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), 1-bromomethyl-2-chloro-benzene (0.123 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-(2-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.035 g, 27%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.94 (s, 2H), 7.16-7.52 (m, 7H), 7.90 (d, 1H).

Sources & evidence

ORD record
ord-236c95e337684e7793cb279b16244652
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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