4-Chloro-6-nitroquinazoline → N-[3-chloro-4-(2-pyridylmethoxy)phenyl]-6-nitro-quinazolin-4-amine

HRID 1397059Notes

Reaction equation

HRID 1397059 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[NH2:19]>C(O)(C)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

4

Reactant 2

HCID 113562574-Chloro-6-nitroquinazolineHCID 167812123-Chloro-4-(2-pyridylmethoxy)aniline

Product 1

HCID 18967699N-[3-chloro-4-(2-pyridylmethoxy)phenyl]-6-nitro-quinazolin-4-amineYield 74.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-nitro-quinazoline 4b crude product (6.06 g, 28.90 mmol) was dissolved in 100 mL of isopropanol, followed by addition of 3-chloro-4-(2-pyridylmethoxy)aniline 4c (7.47 g, 31.8 mmol). The reaction mixture was heated to reflux for 5 hours. The mixture was cooled to room temperature, the solid was precipitated, filtered and the filter cake was washed with ethyl acetate, saturated brine (50 mL) and water (150 mL) successively, dried under vacuum to obtain the title compound N-[3-chloro-4-(2-pyridylmethoxy)phenyl]-6-nitro-quinazolin-4-amine 4d (8.38 g, yield 74.8%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. customthe solid was precipitated
  4. filtrationfiltered
  5. washthe filter cake was washed with ethyl acetate, saturated brine (50 mL) and water (150 mL) successively
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7d9ec69371384f5d886c2771738be331
Source dataset
uspto-grants-2014_12
Patent number
US08901140B2

Reaction notes

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