Ethyl Acetate → HCID 11538371, compound

HRID 2427633Notes

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][CH:15]([NH2:24])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:24]([CH:15]([CH3:14])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.107 g, 0.3 mmol), 1-methyl 3-phenyl-propylamine (0.065 g, 0.4 mmol), and K2CO3 (0.083 g, 0.6 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-(1-methyl-3-phenyl-propyl)-2,3-dihydro-isoindol-1-one (0.098 g, 84%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.32 (d, 3H), 1.94 (m, 2H), 2.54-2.78 (m, 2H), 4.21 (dd, 2H), 4.64 (q, 1H), 7.12-7.24 (m, 6H), 7.41 (d, 1H), 7.88 (d, 1H). GC-MS: m/z 391 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-7083592d77b54549896842e74fd16b05
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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