Bromine → N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromide

HRID 1268729Notes

Reaction equation

HRID 1268729 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Br:26]Br>C(O)(=O)C>[BrH:26].[Br:26][CH:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=1)[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:25]

Participants

4

Reactant 2

HCID 24408BromineHCID 21964221N-[4-[2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide

Product 1

HCID 18446669N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromideYield 180.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-[4-[2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide (19.0 g, 57.5 mmol) in acetic acid (60 mL) was added dropwise bromine (3.0 mL, 57.5 mmol) at room temperature over 1 hr., and the reaction mixture was stirred for 2 hrs. The precipitated crude crystals were collected by filtration and washed with ethyl acetate to give the title compound (25.4 g, yield 90%).

Workup

  1. customThe precipitated crude crystals
  2. filtrationwere collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7861bc5b44304a14b940e1337695a8e5
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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