Hydrochloric Acid → 3-Bromo-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 2405017Notes

Reaction equation

HRID 2405017 reaction equation
F[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[C:21](=[O:26])[NH:22][CH:23]=[CH:24][CH:25]=1.Cl>CS(C)=O.O>[Br:19][C:20]1[C:21](=[O:26])[N:22]([C:2]2[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=2[CH3:12])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8185493-Bromo-2-hydroxypyridineHCID 113672322-Fluoro-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 594102073-Bromo-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

223 g (38% strength, 0.5 mol) of 2-fluoro-1,3-dimethyl-5-nitrobenzene and 138 g (1.0 mol) of potassium carbonate were introduced as initial charge in 1.95 l of DMSO and heated to 120° C. At this temperature, a solution of 100 g (87% purity, 0.5 mol) of 3-bromopyridone in DMSO was added dropwise. The reaction mixture was stirred for 3.5 h at 120° C., cooled to RT, stirred into water, rendered slightly acidic with hydrochloric acid and extracted with ethyl acetate. The aqueous phase was extracted again with ethyl acetate, and the combined organic phases were washed with water, dried over sodium sulphate, filtered and evaporated to dryness on a rotary evaporator. The crude product was purified over silica gel with dichloromethane then ethyl acetate/dichloromethane=1:20. The isolated product was stirred into diethyl ether/petroleum ether=1:1.5, filtered off with suction and washed with petroleum ether. This gave 75.2 g (47%) of the desired product.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous phase was extracted again with ethyl acetate
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness on a rotary evaporator
  8. customThe crude product was purified over silica gel with dichloromethane
  9. stirringThe isolated product was stirred into diethyl ether/petroleum ether=1:1.5
  10. filtrationfiltered off with suction
  11. washwashed with petroleum ether

Sources & evidence

ORD record
ord-b3a6cbc1731f486499f09ec8b3ee6eeb
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

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