Hydrochloric Acid → HCID 86746628, compound

HRID 1613931Notes

Reaction equation

HRID 1613931 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.[CH2:8]([C:17]1[C:26]([CH3:27])=[C:25]([O:28]C(=O)C)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl>CO>[CH2:8]([C:17]1[CH:26]([CH3:27])[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 11430Potassium CarbonateHCID 15007055HCID 15007055, compound

Product 1

HCID 86746628HCID 86746628, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 300 mg (2.17 mmols) of potassium carbonate and 3 ml of water was added to a solution of 705 mg (2.17 mmols) of 2-(trans-2-nonenyl)-3-methyl-4-acetoxyquinoline, 10 ml of water and 50 ml of methanol and stirred at room temperature for 10 minutes. This solution was neutralized with 1N hydrochloric acid, after which the solvent was distilled off under reduced pressure, followed by addition of 50 ml of chloroform, 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 550 mg (yield 90%) of 2-(trans-2-nonenyl)-3-methyl-4-quinolone.

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionfollowed by addition of 50 ml of chloroform
  3. washwashing 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-a5acf91649054757b1ef7f66c40777b3
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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