Benzene → 5(2-Cyanophenyl)indazole

HRID 1938615ノート

反応式

HRID 1938615 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 stream 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 eluted 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 stream 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
  9. washeluted with 50% ether in hexane

出典と根拠

ORDレコード
ord-de088c8441e246b59b7a9f4fced82974
出典データセット
uspto-grants-1997_12
特許番号
US05693633

反応ノート

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