3-Nitro-p-tolualdehyde → HCID 67455030, compound

HRID 1846379Notes

Reaction equation

HRID 1846379 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:32]=[CH:31][CH:30]=[CH:29][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH2:27][CH3:28])[CH3:26])=[CH:21][CH:20]=1)=[O:17]>CCO>[CH:25]([C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C:16](=[O:17])[C:15]3[C:14](=[CH:32][CH:31]=[CH:30][CH:29]=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)([CH2:27][CH3:28])[CH3:26]

Participants

4

Reactant 2

HCID 17989983-Nitro-p-tolualdehydeHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamide

Product 1

HCID 67455030HCID 67455030, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-methyl-3-nitrobenzaldehyde (0.246 g, 1.50 mmol) and anhydrous CuCl2 (0.400 g, 3.00 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.400 g, 1.50 mmol) in anhydrous EtOH (15 mL). After heating at reflux temperature for 2 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-sec-butylphenyl)-2-(4-methyl-3-nitrophenyl)quinazolin-4(3H)-one (0.500 g, 81%).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 2 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-b590529b7e8f4a2994a4199d7b3fac19
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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