Triethylamine → 4-chloro-2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

HRID 606034

Reaction equation

HRID 606034 reaction equation
C(N(CC)CC)C.[CH2:8]([N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([Cl:24])[C:14]=2[N:13]=[C:12]1[CH2:25][O:26][CH2:27][CH3:28])[CH:9]=[CH2:10].[OH:29][N:30]=[C:31](Cl)[CH3:32]>ClCCl>[Cl:24][C:15]1[C:14]2[N:13]=[C:12]([CH2:25][O:26][CH2:27][CH3:28])[N:11]([CH2:8][CH:9]3[O:29][N:30]=[C:31]([CH3:32])[CH2:10]3)[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69633Ethanimidoyl chloride, N-hydroxy-HCID 860914521-allyl-4-chloro-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 866168704-chloro-2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolineYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.04 mL, 7.46 mmol) was added to a 0° C. solution of 1-allyl-4-chloro-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline (1.50 g, 4.97 mmol) and N-hydroxyethanimidoyl chloride (581 mg, 6.21 mmol) in dichloromethane (80 mL). The reaction solution was allowed to warm slowly to room temperature and stir overnight under a nitrogen atmosphere. After 20 hours, the solution was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, elution with 98:2 dichloromethane/methanol) to yield 4-chloro-2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (1.34 g) as a white solid.

Workup

  1. waitAfter 20 hours
  2. washthe solution was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (silica gel, elution with 98:2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-fb28a50943984e76b1da50232fa71d68
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Linked notes

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