m-Chloroperbenzoic acid → N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxide

HRID 2373300Notes

Reaction equation

HRID 2373300 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:2]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH+:11]([O-:36])[C:12](=[O:27])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][CH2:20][C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[N:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9884942Benzamide, N-3-isoquinolinyl-2-[(4-pyridinylmethyl)amino]-

Product 1

HCID 86596455N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxideYield 30.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

212 mg (0.6 mmol) of N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide is mixed in 10 ml of dichloromethane with 103 mg (0.6 mmol) of m-chloroperbenzoic acid, and it is stirred for 6 hours at room temperature in a moisture-free environment and under argon. The batch is then washed with 15 ml of saturated sodium bicarbonate solution and with saturated common salt solution, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride:ethanol=10:1 as an eluant. 68 mg (30% of theory) of N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxide with a melting point of 212.2° C. is obtained.

Workup

  1. washThe batch is then washed with 15 ml of saturated sodium bicarbonate solution and with saturated common salt solution
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-103248b508ed448fb9a9ba4fe149a610
Source dataset
uspto-grants-2008_12
Patent number
US07459470B2

Reaction notes

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