Ethyl Acetate → HCID 11552575, compound

HRID 2427614Notes

Reaction equation

HRID 2427614 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.[C:14]1([CH2:20][CH2:21][CH2:22][NH2:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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:23]([CH2:22][CH2:21][CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 162593-PhenylpropylamineHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 11552575HCID 11552575, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.107 g, 0.3 mmol), 3-phenyl-propylamine (0.071 mL, 0.5 mmol), and K2CO3 (0.138 g, 1 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-phenyl-propyl)-2,3-dihydro-isoindol-1-one (0.054 g, 48%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.01 (m, 2H), 2.72 (t, 2H), 3.66 (t, 2H), 4.25 (s, 2H), 7.14-7.42 (m, 7H), 7.90 (d, 1H).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-6be191472e5446b4815841c97e18edca
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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