Acetic Acid → HCID 135976857, compound

HRID 1939118Notes

Reaction equation

HRID 1939118 reaction equation
C(O)(=O)C.[CH2:5]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([C:25]1[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=1)[CH:19]=[CH:18]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br>O>[CH2:5]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[CH:19]=[CH:18]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 21466811HCID 21466811, compound

Product 1

HCID 135976857HCID 135976857, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 35 ml of acetic acid, 2.5 g of 6-decyl-2-(4-methoxyphenyl)quinoline and 15 ml of 47%-hydrobromic acid were added, followed by stirring for 12 hours at 100° C. and further stirring overnight at room temperature. After the reaction, the reaction mixture was poured into water and subjected to extraction with chloroform. The organic layer was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent and purification by silica gel column chromatography to obtain 1.7 g of 6-decyl-2-(4-hydroxyphenyl)quinoline.

Workup

  1. stirringfurther stirring overnight at room temperature
  2. customAfter the reaction
  3. extractionsubjected to extraction with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationfollowed by distilling-off of the solvent and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-4e12053d4b024fd6ae6e1fecc0fd0bda
Source dataset
uspto-grants-1997_12
Patent number
US05695684

Reaction notes

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