Hydrochloric Acid → HCID 86746626, compound

HRID 1613928Notes

Reaction equation

HRID 1613928 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](/[C:16]1[C:25]([CH3:26])=[C:24]([O:27]C(=O)C)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CO.Cl>O>[CH:7](/[C:16]1[CH:25]([CH3:26])[C:24](=[O:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 15007050HCID 15007050, compound

Product 1

HCID 86746626HCID 86746626, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 ml of an aqueous solution of 6.30 g (45.6 mmols) of potassium carbonate was added to a solution of 2.47 g (7.60 mmols) of 2-(trans-1-nonenyl)-3-methyl-4-acetoxyquinoline, 250 ml of methanol and 50 ml of water and stirred at room temperature for 13 hours. This solution was neutralized with 1N hydrochloric acid, after which the solvent was distilled off under reduced pressure, to which 100 ml of chloroform was added, followed by washing with water and drying with sodium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=1:2) to obtain 1.66 g (yield 77%) of 2-(trans-1-nonenyl)-3-methyl-4-quinolone.

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure, to which 100 ml of chloroform
  2. additionwas added
  3. washby washing with water
  4. dry with materialdrying with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=1:2)

Sources & evidence

ORD record
ord-8568654750f04bbc829edf6646c47c05
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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