N,N-Dimethylaniline → 4-chloro-2-(3-pyridyl)quinazoline

HRID 1648215Notes

Reaction equation

HRID 1648215 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:11]=[CH:10][NH:9][C:7](=O)[C:5]=2[CH:6]=1.C[N:13]([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=CC=1.P(Cl)(Cl)([Cl:23])=O>C1C=CC=CC=1>[Cl:23][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[N:11]=[C:10]([C:17]2[CH:20]=[N:13][CH:14]=[CH:19][CH:18]=2)[N:9]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1354087534(1H)-Quinazolinone

Product 1

HCID 7437644-chloro-2-(3-pyridyl)quinazoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the quinazolinone compound (6.7 g, prepared in Reference example 7) and 5.7 mL of N,N-dimethylaniline in 200 mL of benzene was heated to reflux, under nitrogen atmosphere, for one-half hour with the removal of 15 mL of distillate. After cooling to room temperature, phosphorus oxychloride (4.5 g) was added and the resulting solution heated to reflux for six hours. After cooling to room temperature, the solution was washed with ice water and dilute sodium hydroxide solution. The organic extract was dried over sodium sulfate and concentrated under reduced pressure. The concentrate was triturated in ether and collected to give the title compound (3.0 g) having the following physical data.

Workup

  1. temperatureto reflux, under nitrogen atmosphere, for one-half hour with the removal of 15 mL of distillate
  2. temperaturethe resulting solution heated
  3. temperatureto reflux for six hours
  4. temperatureAfter cooling to room temperature
  5. washthe solution was washed with ice water and dilute sodium hydroxide solution
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was triturated in ether
  10. customcollected

Sources & evidence

ORD record
ord-628f843009cf46b0ac5d482500cab106
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Reaction notes

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