N,N-Dimethylaniline → 4-Chloro-8-nitroquinazoline

HRID 513742

Reaction equation

HRID 513742 reaction equation
CN(C)C1C=CC=CC=1.[N+:10]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][NH:19][C:18]2=O)([O-:12])=[O:11].O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:18]1[C:17]2[C:22](=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[CH:15][CH:16]=2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1354087998-nitroquinazolin-4-ol

Product 1

HCID 114584714-Chloro-8-nitroquinazolineYield 59.63%

Conditions

Temperature
65 °C

Procedure

N, N-dimethylaniline (0.37 ml, 1.23 mmol) was added dropwise to a solution of 8-nitro-3H-quinazolin-4-one 476 (200 mg, 1.04 mmol) in POCl3 (1.25 ml, 10.5 mmol) at 0° C. The mixture was heated at 65° C. for 1.5 h. After cooling, the mixture was concentrated in vacuo. The residue was quenched with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc (25 ml, ×2). The combined organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/DCM (80:20) to give the title compound (130 mg, 59.63%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was quenched with sat. NaHCO3 solution
  4. extractionthe aqueous phase was extracted with EtOAc (25 ml, ×2)
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with n-hexane/DCM (80:20)

Sources & evidence

ORD record
ord-980da24d9af34cc59d13048e1057d417
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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