Acetic Anhydride → HCID 22052544, compound

HRID 1840238Notes

Reaction equation

HRID 1840238 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:10]=2)[N:5]=[C:4]([CH3:17])[C:3]=1[CH3:18].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:10]=2)[N:5]=[C:4]([CH3:17])[C:3]=1[CH3:18])(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178442067HCID 178442067, compound

Product 1

HCID 22052544HCID 22052544, compoundYield 74%

Procedure

100 Milligrams of 4-hydroxy-2,3-dimethyl-6-n-pentyl-quinoline (Compound No. 97) was stirred in 2 ml of acetic anhydride at 120° C. for 4 hours. After the solvent was evaporated, 20 ml of ethyl acetate was added and the reaction mixture was washed with an aqueous saturated sodium hydrogencarbonate solution and a saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-100) eluting with n-hexane/ethyl acetate (5:1) to obtain 87.4 mg of 4-acetoxy-2,3-dimethyl-6-n-pentyl-quinoline (yield 74%). Its NMR spectral data are shown in the following Table 2.

Workup

  1. customAfter the solvent was evaporated
  2. addition20 ml of ethyl acetate was added
  3. washthe reaction mixture was washed with an aqueous saturated sodium hydrogencarbonate solution
  4. dry with materiala saturated brine and dried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-100)
  7. washeluting with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-5fb3f0aea3034de8852f13efe724ba51
Source dataset
uspto-grants-2004_01
Patent number
US06680282B2

Reaction notes

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