Pyridine → 2-(6-Decyloxy-2-naphthoylamino)-4-butylphenol

HRID 5282

Reaction equation

HRID 5282 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[OH:12].[CH2:13]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C:34](Cl)=[O:35])[CH:28]=[CH:27]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O1CCOCC1.N1C=CC=CC=1>O>[CH2:13]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C:34]([NH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[OH:12])=[O:35])[CH:28]=[CH:27]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 146926696-Decyloxy-2-naphthoyl chlorideHCID 150363192-Amino-4-butylphenol

Product 1

HCID 197363202-(6-Decyloxy-2-naphthoylamino)-4-butylphenolYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In a 50 ml three-neck flask, 0.40 g (2.42 m mole) of 2-amino-4-butylphenol, 0.85 g (2.74 m mole) of 6-decyloxy-2-naphthoic acid chloride and 10 ml of dioxane were placed. To the mixture, 0.81 ml of pyridine was added dropwise under stirring at ca. 75° C. of mixture temperature. After the reaction, the reaction mixture was poured into 80 ml of water to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from acetone to obtain 1.00 g of 2-(6-decyloxy-2-naphthoylamino)-4-butylphenol (Yield: 86.5%).

Workup

  1. customAfter the reaction
  2. customto precipitate a crystal
  3. filtrationThe crystal was filtered
  4. washwashed with water
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-1dfcf1ca247542b98a807a6c7678748b
Source dataset
uspto-grants-1993_09
Patent number
US05244596

Linked notes

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