Pyridine → HCID 23354782, compound

HRID 234582Notes

Reaction equation

HRID 234582 reaction equation
Cl.[O:2]=[C:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][NH2:5].[CH2:12]([O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([C:33](Cl)=[O:34])[CH:27]=[CH:26]2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O1CCOCC1.N1C=CC=CC=1>O>[O:2]=[C:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][NH:5][C:33]([C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([O:22][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:24]=2)[CH:29]=1)=[O:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 146926696-Decyloxy-2-naphthoyl chlorideHCID 233547891-Aminooctan-2-one--hydrogen chloride (1/1)

Product 1

HCID 23354782HCID 23354782, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 ml-three-necked flask, 0.20 g (1.11 mM) of 2-oxooctylamine hydrochloride, 0.46 g (1.33 mM) of 6-decyloxy-2-naphthoyl chloride and 5 ml of dioxane were placed. To the mixture, 1.6 ml of pyridine was added at about 85° C. under heat-stirring, followed by heat-stirring for 30 minutes at 92°-94° C. After the reaction, the reaction mixture was poured into water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from a mixture solvent of acetonemethanol to provide 0.41 g of 2-oxooctyl-(6-decyloxy-2-naphthoyl)amine (Yield: 81.2%).

Workup

  1. stirringby heat-stirring for 30 minutes at 92°-94° C
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with water
  6. customfollowed by recrystallization from a mixture solvent of acetonemethanol

Sources & evidence

ORD record
ord-1a999791ac8d4fcf9c76df138c9bbb9d
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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