Ethyl Acetate → HCID 57949667, compound

HRID 2427597Notes

Reaction equation

HRID 2427597 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[CH3:13][CH:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][NH2:16].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH3:13][CH:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][N:16]1[CH2:10][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]1=[O:12]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 12672558beta-Methylbenzenepropanamine

Product 1

HCID 57949667HCID 57949667, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.460 g, 2.0 mmol), 2-methyl-3-phenyl-propylamine (0.298 g, 2.0 mmol), and K2CO3 (0.500 g, 3.6 mmol) in toluene (10 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-(2-methyl-3-phenyl-propyl)-2,3-dihydro-isoindol-1-one (0.265 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.93 (d, 3H), 2.19 (m, 1H), 2.46 (m, 1H), 2.73 (m, 1H) 3.56 (d, 2H), 4.36 (dd, 2H), 7.14-7.56 (m, 8H), 7.86 (d, 1H). GC-MS: m/z 265 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-be51313c3e1e4f24b2ad01e38a3bed2f
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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