Bromine → 3-Bromo-4-methyl-5-nitro-1,2-dihydropyridin-2-one

HRID 508484

Reaction equation

HRID 508484 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][NH:5][C:4](=[O:11])[CH:3]=1.[Br:12]Br>O>[Br:12][C:3]1[C:4](=[O:11])[NH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 3453714-Methyl-5-nitro-1,2-dihydropyridin-2-one

Product 1

HCID 401519143-Bromo-4-methyl-5-nitro-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

In a 1000 ml three-necked round-bottomed flask, 5.00 g of 4-methyl-5-nitro-1H-pyridin-2-one (CA registry number: 21901-41-7) is suspended in 500 ml of water. Under stirring, the mixture is kept at a temperature of 40° C. while 1.83 ml of elemental bromine is added dropwise. Stirring at 40° C. is continued for an additional 4 hours. Afterwards, the mixture is cooled to 10° C. and the resulting precipitate collected by filtration and washed with water (4×). After drying, 6.65 g of the title compound is obtained in the form of a beige solid (MP: 237-240° C.).

Workup

  1. additionis added dropwise
  2. stirringStirring at 40° C.
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water (4×)
  5. customAfter drying

Sources & evidence

ORD record
ord-060f95c1ea164b63ae0bb07e83e11221
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Linked notes

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