Sodium Bicarbonate → HCID 178441048, compound

HRID 1840242Notes

Reaction equation

HRID 1840242 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[C:14]([CH:23]=[O:24])[CH:15]=[C:16]([CH:19]([CH2:21][CH3:22])[CH3:20])[CH:17]=2)[N:12]=[C:11]([CH3:25])[C:10]=1[CH3:26])C1C=CC=CC=1.C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[OH:8][C:9]1[C:18]2[C:13](=[C:14]([CH:23]=[O:24])[CH:15]=[C:16]([CH:19]([CH2:21][CH3:22])[CH3:20])[CH:17]=2)[N:12]=[C:11]([CH3:25])[C:10]=1[CH3:26]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22052555HCID 22052555, compound

Product 1

HCID 178441048HCID 178441048, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

800 Milligrams of the resultant 4-benzyloxy-6-s-butyl-8-formyl-2,3-dimethylquinoline was dissolved in 2.5 ml of 20% sulfuric acid and stirred at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was neutralized with an aqueous saturated sodium hydrogencarbonate solution to produce precipitates, which were washed with water and n-hexane and then dried under reduced pressure to obtain 490 mg of 4-hydroxy-6-s-butyl-8-formyl-2,3-dimethylquinoline. 440 Milligrams of 4-hydroxy-6-s-butyl-8-formyl-2,3-dimethylquinoline was suspended in a mixture of 3 ml of acetic anhydride and 0.5 ml of pyridine and the mixture was stirred at 120° C. for 1.5 hours. The reaction mixture was cooled to room temperature, neutralized with an aqueous saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The resultant organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated, the resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200) eluting with n-hexane/ethyl acetate (10:1) to obtain 220 mg of 4-acetoxy-6-s-butyl-8-formyl-2,3-dimethylquinoline (yield 13%). Its NMR spectral data are shown in the following Table 2.

Workup

  1. temperatureAfter cooling to room temperature
  2. customto produce
  3. customprecipitates
  4. washwhich were washed with water and n-hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a9c843c78c24499fb57cbbf9412961d7
Source dataset
uspto-grants-2004_01
Patent number
US06680282B2

Reaction notes

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