2-amino-N-(4-chlorophenyl)benzamide → HCID 67454597, compound

HRID 1846376Notes

Reaction equation

HRID 1846376 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[CH:29]=[CH:28][CH:27]=[CH:26][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[O:17]>CCO>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C:16](=[O:17])[C:15]3[C:14](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:13]=[C:6]2[C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6704722-amino-N-(4-chlorophenyl)benzamideHCID 17989983-Nitro-p-tolualdehyde

Product 1

HCID 67454597HCID 67454597, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-methyl-3-nitrobenzaldehyde (0.270 g, 1.60 mmol) and anhydrous CuCl2 (0.435 g, 3.20 mmol) were added to a solution of 2-amino-N-(4-chlorophenyl)benzamide (0.400 g, 1.60 mmol) in anhydrous EtOH (10 mL). After heating at reflux temperature for 3 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 60% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(4-methyl-3-nitrophenyl)quinazolin-4(3H)-one (0.400 g, 63%).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 3 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 5% to 60% EtOAc in heptane

Sources & evidence

ORD record
ord-6628f6b1e7ff4c889da635c4434396aa
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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