Sodium Hydroxide → 3-(4-bromophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one

HRID 1846371Notes

Reaction equation

HRID 1846371 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:24]=[CH:23][C:22]([N+]([O-])=O)=[C:21](/[CH:28]=[CH:29]/[N:30](C)C)[CH:20]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CC(O)=O.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:20]=[C:21]3[C:22](=[CH:23][CH:24]=2)[NH:30][CH:29]=[CH:28]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86659823HCID 86659823, compound

Product 1

HCID 866598243-(4-bromophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-oneYield 18%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zn dust (2.0 g, 30.0 mmol) was added to a solution of (E)-3-(4-bromophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one (1.5 g, 3.0 mmol) in AcOH (25 mL). The mixture was stirred at room temperature overnight, then heated to reflux temperature for 1 hour. After cooling to 0° C., the reaction mixture was basified with 1 N NaOH and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 40% EtOAc in CH2Cl2, afforded 3-(4-bromophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one (0.225 g, 18%).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 1 hour
  3. temperatureAfter cooling to 0° C.
  4. extractionextracted with EtOAc
  5. washThe organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 0% to 40% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-0326310b9e5d44bcbc2c89c5e62d800d
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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