2-amino-n-(4-bromophenyl)benzamide → HCID 86659822, compound

HRID 1846369Notes

Reaction equation

HRID 1846369 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[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]([Br:25])=[CH:21][CH:20]=1)=[O:17]>CCO>[Br: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:5]2[C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4788192-amino-n-(4-bromophenyl)benzamideHCID 111945283-Methyl-4-nitrobenzaldehyde

Product 1

HCID 86659822HCID 86659822, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-methyl-4-nitrobenzaldehyde (0.85 g, 5.20 mmol) and anhydrous CuCl2 (2.1 g, 15.5 mmol) were added to a solution of 2-amino-N-(4-bromophenyl)benzamide (1.5 g, 5.20 mmol) in anhydrous EtOH (60 mL). After heating at reflux temperature for 3.5 hours, the 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 15% to 60% EtOAc in heptane, afforded 3-(4-bromophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3H)-one (1.4 g, 62%).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 3.5 hours
  3. concentrationthe 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 15% to 60% EtOAc in heptane

Sources & evidence

ORD record
ord-be573fe1a35c4adfb2bdcf40754ba55a
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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