Water → 3-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

HRID 2405007Notes

Reaction equation

HRID 2405007 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[O:19][CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN1CCCC1=O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[O:19][CH3:20])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 8185493-Bromo-2-hydroxypyridineHCID 144519681-Fluoro-2-methoxy-4-nitrobenzene

Product 1

HCID 594101453-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

36.2 g of 3-bromopyridone (87% purity, 0.18 mol) and 29.4 g of 4-fluoro-3-methoxynitrobenzene (0.17 mol) were introduced as initial charge in 180 ml of N-methylpyrrolidone; 46.1 g of anhydrous potassium phosphate (0.22 mol) were added and the reaction mixture was carried out at 120° C. for 6 h. After cooling to 90° C., water was added and the mixture was cooled to room temperature. The precipitate was filtered off, washed with water and stirred with a methanol/water mixture (1:1). The solid was filtered off, washed and dried in the air. This gave 38.7 g (66%) of the desired target compound.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. filtrationThe solid was filtered off
  5. washwashed
  6. customdried in the air

Sources & evidence

ORD record
ord-3b01d797735648a996d6ff2444dd089e
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

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