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

HRID 2386776Notes

Reaction equation

HRID 2386776 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:14])[CH:2]=[CH2:3].[Cl:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][C:25](Cl)=[O:26].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:25](=[O:26])[CH2:24][C:17]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=3[Cl:15])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 22327520(2-Chloro-4-methoxyphenyl)acetyl chlorideHCID 573460234-(2-propen-1-yl)-2H-1,4-Benzoxazin-3(4H)-one

Product 1

HCID 666972884-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-acetyl]-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In analogy to Example 56, step 1, 4-allyl-4H-benzo[1,4]oxazin-3-one (18.8 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 6:1) to give the title compound (10.6 g) as a white solid. MS (m/e)=372.2 [M+H+].

Workup

  1. customThe crude product was purified by column chromatography (silica gel, heptane/AcOEt 6:1)

Sources & evidence

ORD record
ord-27200ebbaefc478fa73b1c39310bf9bc
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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