Potassium Carbonate → HCID 117770182, compound

HRID 1526382Notes

Reaction equation

HRID 1526382 reaction equation
[Br:1][C:2]1[C:3](O)=[C:4]([C:13]#[N:14])[C:5](=[O:12])[N:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:7]=1.P(Cl)(Cl)([Cl:18])=O.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[C:3]([Cl:18])=[C:4]([C:13]#[N:14])[C:5](=[O:12])[N:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 117769717HCID 117769717, compound

Product 1

HCID 117770182HCID 117770182, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-4-hydroxy-1-isobutyl-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step B (6.6 g) and phosphorus oxychloride (0.126 mL) was heated at 120° C. for 24 hr, and cooled to room temperature. The reaction mixture was poured into water, and the pH was adjusted to 10 with potassium carbonate. The reaction mixture was extracted with ethyl acetate. The extract was washed with washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (4.60 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed
  4. washwith washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-c01e5c0298744a2bbe47cd187d10e0eb
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…