Benzyl Alcohol → 4-benzyloxy-7-methoxy-8-methylquinoline N-oxide

HRID 1692451Notes

Reaction equation

HRID 1692451 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[N+:15]([O-:25])=[CH:14][CH:13]=1.O>CN(C=O)C>[CH2:3]([O:10][C:12]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[N+:15]([O-:25])=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 576079424-Chloro-7-methoxy-8-methylquinoline N-oxide

Product 1

HCID 576079514-benzyloxy-7-methoxy-8-methylquinoline N-oxideYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (973 mg, 60% in mineral oil, 24.3 mmol) was added at 0° C., under inert atmosphere, to benzylalcohol (2.96 mL, 28.6 mmol) in DMF (10 mL). After 5 min at 0° C., the solution was warmed up to room temperature. After 10 min at room temperature, 4-chloro-7-methoxy-8-methylquinoline N-oxide (61, 3.2 g, 14.3 mmol) was added in one potion. The resulting black solution was stirred at room temperature under inert atmosphere for another 30 min, then poured into ice-cooled water, and extracted 4 times with AcOEt. Combined organic layers were dried (Na2SO4) and evaporated. The residue was purified by column chromatography (gradient AcOEt/CH2Cl2, 1:1 to 1:0, then AcOEt/MeOH 9:1) to give 2.5 g (59%) of the target product 62 as a yellow powder: m/z=296 (M+H)+.

Workup

  1. waitAfter 10 min at room temperature
  2. additionpoured into ice-
  3. extractionextracted 4 times with AcOEt
  4. dry with materialCombined organic layers were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography (gradient AcOEt/CH2Cl2, 1:1 to 1:0

Sources & evidence

ORD record
ord-b05c79df620e4bbb8923a48e32b30732
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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