Benzyloxyamine hydrochloride → 2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-ol

HRID 415510Notes

Reaction equation

HRID 415510 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1Cl)=[CH:16][CH:15]=[CH:14][CH:13]=2)=O.Cl.C([O:28][NH2:29])C1C=CC=CC=1>C(O)(C)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:29]([OH:28])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 66620499HCID 66620499, compound

Product 1

HCID 666210712-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-olYield 44.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

A mixture of 5-chloro-N-(4-chloroquinolin-3-yl)pentanamide (1.0 g, 3.365 mmol) and O-benzylhydroxylamine hydrochloride (0.59 g, 3.70 mmol) in 10 mL of isopropanol was heated to 82° C. under an atmosphere of N2. After 2 days the mixture was cooled, solids were filtered off and rinsed with hexane and then ether. The brown solid was dried to give 0.4105 g of 2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-ol.

Workup

  1. temperatureAfter 2 days the mixture was cooled
  2. filtrationsolids were filtered off
  3. washrinsed with hexane
  4. customThe brown solid was dried

Sources & evidence

ORD record
ord-5ec25f415b51427babb7a47e53e7c383
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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