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

HRID 1803671Notes

Reaction equation

HRID 1803671 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-b10d662677be485bb97fab283c990896
Source dataset
uspto-grants-2013_01
Patent number
US08349869B2

Reaction notes

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