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

HRID 1846364ノート

反応式

HRID 1846364 の反応式
[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

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 86659818(E)-3-(4-Chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-458703e9e9494429948c51b96200d68e
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

反応ノート

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