2'-Aminoacetophenone → HCID 475454, compound

HRID 1654545Notes

Reaction equation

HRID 1654545 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9](Br)[CH3:10].[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])=[O:14]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13](=[O:14])[CH3:12])[CH3:10]

Participants

3

Reactant 2

HCID 110862'-AminoacetophenoneHCID 230009212-(1-Bromoethyl)-1,3-dichlorobenzene

Product 1

HCID 475454HCID 475454, compoundYield 16.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 5.5 g of 1,3-dichloro-2-(1-bromoethyl)benzene and 2.9 g of 2-(methylcarbonyl)benzeneamine was stirred for 8 hours at 100° C. After cooling, the reaction mixture was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50). The eluent of the desired fraction was evaporated and the residue was triturated in hexane. The product was filtered off and dried in vacuo at 60° C., yielding 1.05 g (16.2%) of (±)-1-[2-[[1-(2,6-dichlorophenyl)ethyl]amino]phenyl]ethanone; mp. 122.8° C. (comp. 10).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50)
  3. customThe eluent of the desired fraction was evaporated
  4. customthe residue was triturated in hexane
  5. filtrationThe product was filtered off
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-8e01cc3c026849a2a3b511cda4d50bbe
Source dataset
uspto-grants-1995_04
Patent number
US05407961

Reaction notes

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