Phosphorus oxychloride → 4-Chloro-2-(2-methoxyphenyl)quinazoline

HRID 2189194Notes

Reaction equation

HRID 2189194 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:17](O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:18]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178489369HCID 178489369, compound

Product 1

HCID 180716414-Chloro-2-(2-methoxyphenyl)quinazolineYield 93%

Procedure

A solution of 2-(2-methoxy-phenyl)-quinazolin-4-ol (2.94 g, 11.65 mmol) in phosphorus oxychloride (60 mL) was heated to reflux for 4.5 hours. The orange reaction mixture was concentrated and the resulting gum was treated with ice-cold saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (2×200 mL). The organic layers were combined, dried (MgSO4) and concentrated to give the title compound as a yellow solid (2.92 g, 93%).

Workup

  1. temperatureto reflux for 4.5 hours
  2. concentrationThe orange reaction mixture was concentrated
  3. additionthe resulting gum was treated with ice-cold saturated sodium bicarbonate (200 mL)
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c155d7a0121f4364b9a32c37351709ea
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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