2-amino-N-(4-chlorophenyl)benzamide → HCID 67455493, compound

HRID 1846362Notes

Reaction equation

HRID 1846362 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]([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: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 6704722-amino-N-(4-chlorophenyl)benzamideHCID 111945283-Methyl-4-nitrobenzaldehyde

Product 1

HCID 67455493HCID 67455493, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-methyl-4-nitro-benzaldehyde (0.268 g, 1.60 mmol) and anyhydrous CuCl2 (0.437 g, 3.20 mmol) were added to a solution of 2-amino-N-(4-chlorophenyl)benzamide (0.400 g, 1.60 mmol) in anyhydrous EtOH (15 mL) and heated at reflux temperature for 3.5 hours. After concentration in vacuo and dissolving the residue in EtOAc, the organics were washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 70% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3H)-one (0.300 g, 48%).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 3.5 hours
  3. concentrationAfter concentration in vacuo
  4. dissolutiondissolving the residue in EtOAc
  5. washthe organics were washed 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 10% to 70% EtOAc in heptane

Sources & evidence

ORD record
ord-dfef2c3f5ede4a928c78a1f7dcb42de2
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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