Bromine → 2-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide

HRID 917676Notes

Reaction equation

HRID 917676 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:4][CH:3]=1.[Br:21]Br>C(O)(=O)C>[BrH:21].[Br:21][CH:9]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[CH:13]2)[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:20]

Participants

4

Reactant 2

HCID 24408BromineHCID 688842031-(6-Methylpyridin-2-YL)-2-(quinolin-6-YL)ethanone

Product 1

HCID 865927622-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromideYield 189%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone (1.0 g, 3.81 mmol) in acetic acid (15 mL) was slowly added a solution of bromine (0.194 ml, 3.81 mmol, 1 equiv) in acetic acid (5 mL) over 5 minutes. After stirring at the ambient temperature for 3 hours the reaction mixture was concentrated in vacuo, and to the residue dichloromethane (10 mL) and ether (60 mL) were added successively. The resulting mixture was stirred during 18 hours. The solid was filtered off and dried in vacuo, which provided 2-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide (1.52 g, 95%).

Workup

  1. concentrationwas concentrated in vacuo
  2. additionto the residue dichloromethane (10 mL) and ether (60 mL) were added successively
  3. stirringThe resulting mixture was stirred during 18 hours
  4. filtrationThe solid was filtered off
  5. customdried in vacuo, which

Sources & evidence

ORD record
ord-769d17c804c3481e909f38b022c4cd1c
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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