Quinoline 1-oxide → HCID 178518913, compound

HRID 1987645Notes

Reaction equation

HRID 1987645 reaction equation
[CH2:1]([C:8]1[CH2:12][C:11](=[O:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:14]1([O-])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C(OC(=O)C)(=O)C>[CH2:1]([C:8]1=[N:9][NH:10][C:11](=[O:13])/[C:12]/1=[C:15]1\[NH:14][C:23]2[C:18]([CH:17]=[CH:16]\1)=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15366Quinoline 1-oxideHCID 220592713-benzyl-1H-pyrazol-5(4H)-one

Product 1

HCID 178518913HCID 178518913, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-benzyl-1H-pyrazol-5(4H)-one (0.234 g, 1.34 mmol) and quinoline N-oxide (0.24 g, 1.34 mmol) were stirred in acetic anhydride (1.5 mL) at ambient temperature for 20-30 minutes. The reaction mixture was concentrated and the resulting solid filtered off and washed with a minimum amount of ether to yield the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.76 (s, 2H) 3.98 (bs, 1H) 7.23-7.29 (m, 6H) 7.61 (t, J=7.58 Hz, 1H) 7.76-7.82 (m, 1H) 7.93 (d, J=8.34 Hz, 1H) 8.08-8.18 (m, 2H); ESI-MS: m/z calc'd for C19H15N3O 301.12. found 302.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe resulting solid filtered off
  3. washwashed with a minimum amount of ether

Sources & evidence

ORD record
ord-fc856b3c01424b0096c9ccc08e4379d7
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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