Thionyl Chloride → 4-Acetoxy-6-s-butyl-8-chloromethyl-2,3-dimethylquinoline

HRID 1840245Notes

Reaction equation

HRID 1840245 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([CH2:19]O)[CH:11]=[C:12]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH:13]=2)[N:8]=[C:7]([CH3:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2].S(Cl)([Cl:25])=O>>[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([CH2:19][Cl:25])[CH:11]=[C:12]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH:13]=2)[N:8]=[C:7]([CH3:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 220525404-Acetoxy-6-s-butyl-8-hydroxymethyl-2,3-dimethylquinoline

Product 1

HCID 220525464-Acetoxy-6-s-butyl-8-chloromethyl-2,3-dimethylquinolineYield 23.5%

Procedure

50 Milligrams of 4-acetoxy-6-s-butyl-8-hydroxymethyl-2,3-dimethylquinoline obtained in Example 34 was dissolved in 0.3 ml of thionyl chloride and stirred at room temperature for 4.5 hours. After thionyl chloride was evaporated under reduced pressure, 0.5 ml of acetic anhydride was added to the resultant crude product and the mixture was stirred at 120° C. for 2 hours. After acetic anhydride was evaporated under reduced pressure, the resultant residue was purified by column chromatography on silica gel (WAKOGEL® C-200) eluting with n-hexane/ethyl acetate (20:1) to obtain 12.5 mg of 4-acetoxy-6-s-butyl-8-chloromethyl-2,3-dimethylquinoline (yield 23.5%). Its NMR spectral data are shown in the following Table 2.

Workup

  1. customAfter thionyl chloride was evaporated under reduced pressure, 0.5 ml of acetic anhydride
  2. additionwas added to the resultant crude product
  3. stirringthe mixture was stirred at 120° C. for 2 hours
  4. customAfter acetic anhydride was evaporated under reduced pressure
  5. customthe resultant residue was purified by column chromatography on silica gel (WAKOGEL® C-200)
  6. washeluting with n-hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-eaeba1bd58d34f1a91264783ee11bb2e
Source dataset
uspto-grants-2004_01
Patent number
US06680282B2

Reaction notes

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