Ethyl Acetate → HCID 57949584, compound

HRID 2427601Notes

Reaction equation

HRID 2427601 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[CH:13]1([CH2:19][NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH:13]1([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])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 76688CyclohexanemethylamineHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 57949584HCID 57949584, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.230 g, 1 mmol), C-cyclohexyl-methylamine (0.190 g, 1 mmol), and K2CO3 (0.230 g, 1.67 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-cyclohexylmethyl-2,3-dihydro-isoindol-1-one (0.085 g, 37%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.18 (m, 5H), 1.72 (m, 6H), 3.46 (d, 2H), 4.38 (s, 2H) 7.42-7.53 (m, 3H), 7.85 (d, 1H). GC-MS: m/z 229 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-5665426c4f5d4c708ccd86afea1df31c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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