Benzyloxyamine hydrochloride → HCID 66620013, compound

HRID 415515Notes

Reaction equation

HRID 415515 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1Cl)=[CH:14][CH:13]=[CH:12][CH:11]=2)=O.Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)(C)C>[CH2:19]([O:26][N:27]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:4]1[CH2:3][CH2:2][Cl:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 66619827HCID 66619827, compound

Product 1

HCID 66620013HCID 66620013, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-chloro-N-(4-chloroquinolin-3-yl)propanamide (1.682 g, 6.243 mmol) and O-benzylhydroxylamine hydrochloride (1.10 g, 6.87 mmol) in 60 mL of isopropanol was heated to 40° C. under an atmosphere of N2. After 25 hours the mixture was cooled, solids were filtered off and rinsed with hexane. Chromatography (SiO2, 8-100% EtOAc/dichloromethane) gave 0.6308 g of 1-(benzyloxy)-2-(2-chloroethyl)-1H-imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. temperatureAfter 25 hours the mixture was cooled
  2. filtrationsolids were filtered off
  3. washrinsed with hexane

Sources & evidence

ORD record
ord-0c156e8445764c85a0cb728cd5021f03
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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