Benzene → 5(2-Cyanophenyl)indazole

HRID 743895Notes

Reaction equation

HRID 743895 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 214688445(2-Cyanophenyl)indazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
45 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-4e9c441473ab4dd8a6ea39439e8daff6
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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