Benzene → 5(2-Cyanophenyl)indazole

HRID 743895ノート

反応式

HRID 743895 の反応式
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])=[CH:7][C:6]=1[CH3:19])C(C)=O.[N+:20]([O-])(O)=O.N([O-])=O.[Na+].C1C=CC=CC=1>C(O)(=O)C.[Cl-].[Na+].O>[C:13]([C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][CH:9]=1)[NH:1][N:20]=[CH:19]2)#[N:14]

参加物

7

反応物 4

HCID 241BenzeneHCID 944Nitric AcidHCID 214688382-(4-Acetamino-3-methylphenyl)benzonitrileHCID 23668193Sodium Nitrite

生成物 1

HCID 214688445(2-Cyanophenyl)indazole

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
45 °C

実験手順

2-(4-Acetamino-3-methylphenyl)benzonitrile (15.2 mmole, 3.8 g) was dissolved in 50 ml acetic acid and treated for 1 hour at room temperature with a scream of gaseous N2O5 generated by the addition of nitric acid to sodium nitrite. Benzene and brine were added to the reaction. The organic layer was separated, dried and warmed gently on a rotorvap (45° C.) for 1 hour. The solution was concentrated. Ether and saturated sodium bicarbonate were added. The organic phase was dried and concentrated. The residue was chromatographed over silica gel eluded with 50% ether in hexane to yield 240 mg of 5(2-cyanophenyl)indazole. (MS)

後処理

  1. additiontreated for 1 hour at room temperature with a scream of gaseous N2O5
  2. customThe organic layer was separated
  3. customdried
  4. concentrationThe solution was concentrated
  5. additionEther and saturated sodium bicarbonate were added
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel

出典と根拠

ORDレコード
ord-4e9c441473ab4dd8a6ea39439e8daff6
出典データセット
uspto-grants-1996_09
特許番号
US05556981

反応ノート

読み込み中…