N-bromobutanimide → 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one

HRID 1921306Notes

Reaction equation

HRID 1921306 reaction equation
[CH2:1]([C:3]1[C:4](=[O:10])[NH:5][C:6]([CH3:9])=[CH:7][CH:8]=1)[CH3:2].[Br:11]N1C(=O)CCC1=O>CO>[Br:11][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[C:4](=[O:10])[NH:5][C:6]=1[CH3:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27978763-ethyl-6-methyl-1H-pyridin-2-one

Product 1

HCID 207792745-bromo-3-ethyl-6-methyl-1H-pyridin-2-oneYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 neck round bottom flask, equipped with an overhead stirrer is charged with 3-ethyl-6-methyl-1H-pyridin-2-one (33.45 g, 0.26 mol) obtained from Step 1 as described above, N-bromosuccinimide (48.6 g, 0.273 mol) and methanol (867 mL) and the mixture stirred at ambient temperature for 17 hr. The mixture is then concentrated to a volume of 200 mL, diluted with water (600 mL) and the resulting suspension is chilled in an ice bath. The solids are collected by filtration, washed with water (300 mL) and dried in a vacuum oven at 64° C. for 24 hr to afford 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one (53.56 g, 95.3% yield) as an off white solid. LC/MS: MS m/e=215/217 (M+H), RT 2.64 min.

Workup

  1. customA 2 neck round bottom flask, equipped with an overhead stirrer
  2. concentrationThe mixture is then concentrated to a volume of 200 mL
  3. additiondiluted with water (600 mL)
  4. temperaturethe resulting suspension is chilled in an ice bath
  5. filtrationThe solids are collected by filtration
  6. washwashed with water (300 mL)
  7. customdried in a vacuum oven at 64° C. for 24 hr

Sources & evidence

ORD record
ord-1974514fad83471dbd5c89f2e9508d13
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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