Benzylamine → HCID 57949794, compound

HRID 2427611Notes

Reaction equation

HRID 2427611 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[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.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH2:14]([N:21]1[CH2:11][C:5]2[C:4](=[CH:9][C:8]([Cl:10])=[CH:7][CH:6]=2)[C:3]1=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 51358462Methyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 57949794HCID 57949794, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-5-chloro-benzoic acid methyl ester (0.200 g, 0.76 mmol), benzylamine (0.135 mL, 1.25 mmol), and K2CO3 (0.276 g, 3.5 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 2-benzyl-6-chloro-2,3-dihydro-isoindol-1-one (0.118 g, 60%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.23 (s, 2H), 4.68 (s, 2H), 7.29 (m, 7H), 7.76 (d, 1H). GC-MS: m/z 257 (M)+, 180 (M−77)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-57b09f472ac5484ea83bea17f219d21c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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