Benzyloxyamine hydrochloride → HCID 86758705, compound

HRID 2298984Notes

Reaction equation

HRID 2298984 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:35])([C:29]2[N:30]([CH3:34])[CH:31]=[N:32][CH:33]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=[C:12]3[C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH:24]=O)=[CH:4][CH:3]=1.Cl.[CH2:37]([O:44][NH2:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.CO>[CH2:37]([O:44][N:45]=[CH:24][C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([C:12]2[C:11]3[C:16](=[CH:17][CH:18]=[C:9]([C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)([OH:35])[C:29]4[N:30]([CH3:34])[CH:31]=[N:32][CH:33]=4)[CH:10]=3)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=2)[CH:22]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 18379017HCID 18379017, compound

Product 1

HCID 86758705HCID 86758705, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-{6-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl}-benzaldehyde (202 mg, 0.418 mMol) was dissolved in a solution of DCM (2.0 mL) and MeOH (2.0 mL) under an atmosphere of dry N2. To this solution was added O-benzylhydroxylamine hydrochloride (66.8 mg, 418 mMol) and the mixture was stirred for 24 hours at ambient temperature. The reaction mixture was concentrated under vacuum and was purified by radial chromatography eluting with MeOH/EtOAc/NH4OH (5:95:0.1) to give the titled compound as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customwas purified by radial chromatography
  3. washeluting with MeOH/EtOAc/NH4OH (5:95:0.1)

Sources & evidence

ORD record
ord-192f6c42d594475181990068da10b4ae
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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