Ethyl Acetate → HCID 57949383, compound

HRID 2427587Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[CH3:13][CH:14]([NH2:23])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH3:13][CH:14]([N:23]1[CH2:10][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]1=[O:12])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 1-methyl-3-phenyl-propylamine (0.090 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(1-methyl-3-phenyl-propyl)-2,3-dihydro-isoindol-1-one (0.072 g, 54%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.32 (d, 3H), 1.92 (m, 2H), 2.64 (m, 2H), 4.34 (dd, 2H), 4.62 (m, 1H), 7.14-7.58 (m, 8H), 7.89 (d, 1H). GC-MS: m/z 265 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-0f8fb4c919db4c8daee7c262057cdd42
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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