Sodium Hydroxide → HCID 77230829, compound

HRID 921032Notes

Reaction equation

HRID 921032 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1([C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15](=O)[NH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.CN(C)C1C=CC=CC=1>[C:6]1([C:12]2[CH:13]=[N:14][C:15]([Cl:3])=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 15293173HCID 15293173, compound

Product 1

HCID 77230829HCID 77230829, compound

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineCatalystHCID 1140TolueneSolvent2×

Procedure

12.1 ml (130 mmol) of phosphoryl chloride are added dropwise at room temperature to a suspension of 22.2 g (100 mmol) of 8-phenyl-1,6-naphthyridin-5(6H)-one [173773-04-1] in 100 ml of toluene. After addition of 5 drops of N,N-dimethylaniline, the reaction mixture is heated under reflux for 5 h. After cooling, the reaction mixture is diluted with 300 ml of toluene, poured onto 1000 g of ice and rendered alkaline (pH about 9) by addition of 5 N NaOH. The organic phase is separated off, washed once with 300 ml of sat. sodium chloride solution, dried over magnesium sulfate, and the toluene is removed in vacuo. Yield: 22.9 g (95 mmol), 95%. Purity: >95% according to 1H-NMR.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling
  4. customThe organic phase is separated off
  5. washwashed once with 300 ml of sat. sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe toluene is removed in vacuo

Sources & evidence

ORD record
ord-6c74a9b51b614da693d32513af908d9b
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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