4-Hydroxy-3-methylbenzaldehyde → 3-(4-chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one

HRID 1846331Notes

Reaction equation

HRID 1846331 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:10].[NH2:11][C:12]1[CH:27]=[CH:26][CH:25]=[CH:24][C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:15]>CCO>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([N:16]2[C:14](=[O:15])[C:13]3[C:12](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:11]=[C:6]2[C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([CH3:10])[CH:4]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 6704722-amino-N-(4-chlorophenyl)benzamide

Product 1

HCID 1363309563-(4-chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-oneYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous CuCl2 (0.306 g, 2.20 mmol) and 4-hydroxy-3-methylbenzaldehyde (0.155 g, 1.10 mmol) were added to a solution of 2-amino-N-(4-chlorophenyl)benzamide (0.280 g, 1.10 mmol) in anhydrous EtOH (10 mL). The mixture was heated at reflux temperature for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 50% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one (0.230 g, 57%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 5% to 50% EtOAc in heptane

Sources & evidence

ORD record
ord-828f3c47c2594f68912968a7ca13be20
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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