Benzene → 5(2-Cyanophenyl)indazole

HRID 976590Notes

Reaction equation

HRID 976590 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 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 rotoryvap (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)

Workup

  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

Sources & evidence

ORD record
ord-179c62b0bcfb4766847edd3b41c9e60e
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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