Ethyl Acetate → HCID 57949369, compound

HRID 2427586Notes

Reaction equation

HRID 2427586 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[C:13]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[C:13]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:14]=[CH:15][C:16]([CH2:19][N:20]2[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:12])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3449894-PhenylbenzylamineHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 57949369HCID 57949369, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), C-biphenyl-4-yl-methylamine (0.110 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-biphenyl-4-ylmethyl-2,3-dihydro-isoindol-1-one (0.079 g, 53%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.26 (s, 2H), 4.84 (s, 2H), 7.32-7.56 (m, 12H), 7.89 (d, 1H). GC-MS: m/z 299 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-82ca898418b345299158e3ae72f9ed48
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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