Ethyl Acetate → 7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one

HRID 2427604Notes

Reaction equation

HRID 2427604 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:23]([CH:21]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)[CH3:22])[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 978031-(4-Chlorophenyl)ethylamineHCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 579497997-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-oneYield 86.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-chloro-benzoic acid methyl ester (0.132 g, 0.5 mmol), 1-(4-chlorophenyl)-ethylamine (0.117 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.132 g, 86%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.66 (d, 3H), 3.95 (d, 1H), 4.34 (d, 1H), 5.84 (q, 1H) 7.26-7.46 (m, 7H). GC-MS: m/z 306 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-51ce4709364c45ecb0871d26d31c78df
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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