m-Chloroperbenzoic acid → HCID 178526246, compound

HRID 990983Notes

Reaction equation

HRID 990983 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[CH2:14][CH2:13][C:12]4[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=4[C:10]=3[NH:9][N:8]=2)=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:25]>O1CCCC1>[NH:9]1[C:10]2[C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[CH2:13][CH2:14][C:15]=2[C:7]([C:4]2[CH:3]=[CH:2][N+:1]([O-:25])=[CH:6][CH:5]=2)=[N:8]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1043374,5-Dihydro-3-(pyridin-4-yl)-2H-benz(g)indazole

Product 1

HCID 178526246HCID 178526246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
57.5 °C

Procedure

3-(4-Pyridyl)-4,5-dihydro-1H-benzo[g]indazole (100 mg, compound commercially available from Aldrich) was dissolved in tetrahydrofuran (5-10 ml) with warming and then 3-chloroperoxybenzoic acid (1.25 molar equivalents of 70-75% pure material) was added. The mixture was heated at 55-60° C. for 4 hours. A precipitate was collected by filtration, washed with tetrahydrofuran and then ether to give 4-(4,5-dihydro-1H-benzo[g]indazol-3-yl)pyridine 1-oxide.

Workup

  1. temperaturewith warming
  2. filtrationA precipitate was collected by filtration
  3. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-a720b48443fa4edc827702afcf682895
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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