2-Methylbenzylamine → 7-Iodo-2-(2-methyl-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427625Notes

Reaction equation

HRID 2427625 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][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].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:18]([CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[CH3:14])[CH2:11]2

Participants

7

Reactant 4

HCID 69932-MethylbenzylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 579497837-Iodo-2-(2-methyl-benzyl)-2,3-dihydro-isoindol-1-oneYield 51.4%

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), 2-methyl-benzylamine (0.063 mL, 0.5 mmol), and K2CO3 (0.138 g, 1.0 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-iodo-2-(2-methyl-benzyl)-2,3-dihydro-isoindol-1-one (0.056 g, 51%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.35 (s, 3H), 4.14 (s, 2H), 4.82 (s, 2H), 7.11-7.38 (m, 6H), 7.91 (d, 1H). GC-MS: m/z 363 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-f6ea688743d44ec69fdc0ee46e1204c0
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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