Benzyloxyamine hydrochloride → 2-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-1-ol

HRID 415506Notes

Reaction equation

HRID 415506 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1Cl)=[CH:15][CH:14]=[CH:13][CH:12]=2)=O.[ClH:19].C([O:27][NH2:28])C1C=CC=CC=1>C(O)(C)C>[Cl:19][CH2:2][CH2:3][CH2:4][C:5]1[N:28]([OH:27])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 66620617HCID 66620617, compound

Product 1

HCID 666207312-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-1-olYield 112%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

A mixture of 4-bromo-N-(4-chloroquinolin-3-yl)butanamide (2.090 g, 6.379 mmol) and O-benzylhydroxylamine hydrochloride (1.527 g, 9.569 mmol) in 20 mL of isopropanol was heated to 82° C. under an atmosphere of N2. After 18 hours the solution was cooled, solids were filtered off and rinsed with ether. The brown solid was dried to give 1.87 g of 2-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-1-ol.

Workup

  1. temperatureAfter 18 hours the solution was cooled
  2. filtrationsolids were filtered off
  3. washrinsed with ether
  4. customThe brown solid was dried

Sources & evidence

ORD record
ord-dbd22715d8e6494d97a13d45db1e1365
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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