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

HRID 1846364Notes

Reaction equation

HRID 1846364 reaction equation
[Cl: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]>[Cl: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 86659818(E)-3-(4-Chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one

Product 1

HCID 468423083-(4-chlorophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-oneYield 39%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zn dust (0.220 g, 3.35 mmol) was added to a solution of (E)-3-(4-chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one in AcOH (15 mL). After heating and stirring at reflux temperature for 4 hours, the mixture was basified with 1N 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 20% to 90% EtOAc in heptane, afford the title compound as a white solid (0.048 g, 39%). 1H-NMR (300 MHz, DMSO-d6): δ11.19 (s, 1H), 8.18-8.21 (m, 1H), 7.88-8.00 (m, 1H), 7.75 (d, J=7.7 Hz, 1H), 7.47-7.70 (m, 2H), 7.30-7.44 (m, 5H), 7.20 (d, J=8.4 Hz, 1H), 7.06 (d, J=6.8 Hz, 1H), 6.40 (d, J=2.0 Hz, 1H). MS (APCI) m/z: 372 (M+H)+.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 4 hours
  3. extractionextracted with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 20% to 90% EtOAc in heptane

Sources & evidence

ORD record
ord-458703e9e9494429948c51b96200d68e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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