Ethyl Acetate → 7-Iodo-2-[3-(4-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one

HRID 2427621Notes

Reaction equation

CO[C:3](=[O:13])[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[I:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:25]([CH2:24][CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=1)[CH2:11]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.245 g, 0.7 mmol), 3-(4-methoxy-phenyl)-propylamine (0.132 g, 0.8 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 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-iodo-2-[3-(4-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.125 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.01 (m, 2H), 2.63 (t, 2H), 3.64 (t, 2H), 3.79 (s, 3H), 4.24 (s, 2H), 6.80 (d, 2H), 7.08-7.44 (m, 4H), 7.90 (d, 1H). GC-MS: m/z 407 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-27c26a46d8e446e085b37e04e6118172
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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