Benzyloxyamine hydrochloride → HCID 57429983, compound

HRID 1845726Notes

Reaction equation

HRID 1845726 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][O:15][CH2:16][CH3:17].Cl.[CH2:20]([O:27][NH2:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(O)C>[CH2:20]([O:27][N:28]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[C:13]1[CH2:14][O:15][CH2:16][CH3:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57429982HCID 57429982, compound

Product 1

HCID 57429983HCID 57429983, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(4-chloroquinolin-3-yl)-2-ethoxyacetamide (4.5 g, 18 mmol) and O-benzylhydroxylamine hydrochloride (4.3 g, 27 mmol) in propan-2-ol (100 mL) was heated at 60° C. for 2 days. The mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 mL) and saturated aqueous sodium bicarbonate (35 mL). The organic layer was dried over potassium carbonate, filtered, and evaporated to yield 5.7 g of crude 1-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline that was used directly in Part B.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (150 mL) and saturated aqueous sodium bicarbonate (35 mL)
  3. dry with materialThe organic layer was dried over potassium carbonate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9b7e6c6515d449d6a80ff7eeeccb0005
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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