Aluminum(III) Chloride → 6-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

HRID 2386762Notes

Reaction equation

HRID 2386762 reaction equation
[CH2:1]([N:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]1=[O:13])[CH3:2].[Cl:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[CH2:23][C:24](Cl)=[O:25].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[CH2:23][C:24]([C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][C:4](=[O:13])[N:3]([CH2:1][CH3:2])[C:8]=2[CH:9]=1)=[O:25]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 138630252H-1,4-Benzoxazin-3(4H)-one, 4-ethyl-HCID 22327520(2-Chloro-4-methoxyphenyl)acetyl chloride

Product 1

HCID 666972646-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In analogy to Example 56, step 1, 4-ethyl-4H-benzo[1,4]oxazin-3-one (10.2 g) was reacted with (2-chloro-4-methoxy-phenyl)-acetyl chloride and AlCl3 in 1,2-dichloroethane 3 h at 0° C. The crude product was purified by column chromatography (silica gel, heptane/AcOEt 2:1) to give the title compound (12.3 g) as a white solid. MS (m/e)=360.1 [M+H+]

Workup

  1. customThe crude product was purified by column chromatography (silica gel, heptane/AcOEt 2:1)

Sources & evidence

ORD record
ord-bdcbb6fb1601476186afe61cc15ff670
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

Loading…