Phthalimidine → HCID 57949650, compound

HRID 2427576Notes

Reaction equation

HRID 2427576 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][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[O:14]([CH2:13][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])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 57949650HCID 57949650, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydroisoindol-1-one (0.066 g, 0.5 mmol,), 2-(bromoethoxy)benzene (0.121 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-phenoxy-ethyl)-2,3-dihydro-isoindol-1-one (0.099 g, 78%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.05 (t, 2H), 4.26 (t, 2H), 4.64 (s, 2H), 6.92 (m, 3H), 7.22-7.60 (m, 5H), 7.88 (d, 1H), GC-MS: m/z 253 (M)+.

Sources & evidence

ORD record
ord-f91e931f7e4e44ce8e036e012d08aa3c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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