Ethyl Acetate → HCID 11710302, compound

HRID 2427608Notes

Reaction equation

HRID 2427608 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[CH:14]1[C:23]2[O:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[O:19][C:18]=2[CH:17]=[CH:16][C:15]=1[CH2:28][NH2:29].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:29]([CH2:28][C:15]1[CH:16]=[CH:17][C:18]3[O:19][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[O:22][C:23]=3[CH:14]=1)[CH2:11]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoateHCID 67252285HCID 67252285, compound

Product 1

HCID 11710302HCID 11710302, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-6-chloro-benzoic acid methyl ester (0.148 g, 0.6 mmol), C-dibenzo[1,4]dioxin-2-yl-methylamine (0.213 g, 1.0 mmol), and K2CO3 (0.207 g, 1.5 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 7-Chloro-2-dibenzo[1,4]dioxin-2-ylmethyl-2,3-dihydro-isoindol-1-one (0.023 g, 13%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.34 (s, 2H), 4.65 (s, 2H), 6.85 (m, 8H), 7.40 (t, 2H). GC-MS: m/z 363 (M)+.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-f6c084e953704fa78db8d5d65682e63e
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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