4-Chloroaniline → HCID 21098392, compound

HRID 1351185Notes

Reaction equation

HRID 1351185 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][NH:7][C:6]2=O.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>O=S(Cl)Cl.CN(C=O)C>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[C:4]=3[N+:16]([O-:18])=[O:17])[N:9]=[CH:8][N:7]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 135513647HCID 135513647, compound

Product 1

HCID 21098392HCID 21098392, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6,7-dimethoxy-5-nitro-3H-quinazolin-4-one (0.5 g, 1.99 mmol) (from Example 1, Step A, supra) in SOCl2 (20 mL) (Aldrich) was added a few drops of DMF (0.05 mL). The reaction mixture was then heated with stirring at 90° C. for 3 hours. The solvents were evaporated and the residue was dried in vacuo. This residue was dissolved in 2-propanol (30 mL), then 4-chloroaniline (0.25 g, 1.99 mmol) (Aldrich) was added. The reaction mixture was heated at 110° C. for 3 hours. The solvents were removed and the residue was purified by chromatography using EtOAc/CH2Cl2/NEt3 (1:2:0.05) as eluent to give the desired (4-chloro-phenyl)-(6,7-dimethoxy-5-nitro-quinazolin-4-yl)-amine as a yellow solid. (Yield 0.5 g, 70%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. customThe solvents were evaporated
  3. customthe residue was dried in vacuo
  4. dissolutionThis residue was dissolved in 2-propanol (30 mL)
  5. temperatureThe reaction mixture was heated at 110° C. for 3 hours
  6. customThe solvents were removed
  7. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-2d44c947eccb4102bfe69aaab0cf09ae
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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