Water → HCID 22052556, compound

HRID 1831724Notes

Reaction equation

HRID 1831724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[C:6]([CH3:14])=[C:5]2[OH:15].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:15][C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)[N:8]=[C:7]([CH3:13])[C:6]=1[CH3:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178432092HCID 178432092, compound

Product 1

HCID 22052556HCID 22052556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

26.6 Grams of 6-bromo-4-hydroxy-2,3,8-trimethylquinoline synthesized in the same way as that described in Example 1 was suspended in 70 ml of dimethylformamide, to which 4.4 g of 60% sodium hydride was added under cooling with ice and then the mixture was stirred at room temperature for 30 minutes. 19 Grams of benzyl bromide was added dropwise to the reaction mixture under cooling with ice and the mixture was allowed to react at room temperature overnight. After 50 ml of water was added, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate overnight. After the solvent was evaporated under reduced pressure, the resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200) eluting with n-hexane/ethyl acetate (6:1) to obtain 24.3 g of 4-benzyloxy-6-bromo-2,3,8-trimethylquinoline.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. customto react at room temperature overnight
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with a saturated brine
  7. dry with materialdried over anhydrous sodium sulfate overnight
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200)
  10. washeluting with n-hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-4eab9b3de7bf44b7b0d9fde05df4ca89
Source dataset
uspto-grants-2006_06
Patent number
US07067668B2

Reaction notes

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