Benzylamine → HCID 57949488, compound

HRID 2427634Notes

Reaction equation

HRID 2427634 reaction equation
CO[C:3](=O)[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=[O:23].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH2:14]([N:21]1[CH2:3][C:4]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[I:10])[C:11]1=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Product 1

HCID 57949488HCID 57949488, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.708 g, 2.0 mmol), benzylamine (0.218 mL, 2.0 mmol), and K2CO3 (0.69 g, 5.0 mmol) in toluene (6 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-benzyl-4-iodo-2,3-dihydro-isoindol-1-one (0.325 g, 47%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.18 (s, 2H), 4.84 (s, 2H), 7.21-7.38 (m, 6H), 7.86 (m, 2H). GC-MS: m/z 349 (M)+, 272 (M−77)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-db1497fce5b94d59b6c5aeb2ca4cac09
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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