Bromide ion → HCID 84689561, compound

HRID 883863Notes

Reaction equation

HRID 883863 reaction equation
[CH:1]([C:4]1[NH:9][C:8](=O)[C:7]([C:11]#[N:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br-:13].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>C1(C)C=CC=CC=1>[Br:13][C:8]1[N:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[C:11]#[N:12]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 105831136-Isopropyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 84689561HCID 84689561, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of the product of Example 12B (4.35 g, 0.0269 mol), tertrabutylammonium bromide (10.4 g, 0.0323 mol) and phosphorous pentoxide (8.01 g, 1.05 mol) in toluene (80 mL) was heated under reflux for 5 hours. The reaction mixture was then cooled to room temperature, water (80 mL) was added, and the mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with toluene (20 mL) and the organic layer separated. The aqueous layer was washed with toluene (50 mL) and the combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title product as a yellow oil (5.64 g, 93%).

Workup

  1. temperatureunder reflux for 5 hours
  2. customthe organic layer separated
  3. washThe aqueous layer was washed with toluene (50 mL)
  4. washthe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cb9486e9204f485baa273ed9cc7ca4f4
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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