Pyridine → HCID 13255813, compound

HRID 978103Notes

Reaction equation

HRID 978103 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:9])=[C:6]([CH:8]=1)[NH2:7].N1C=CC=CC=1.[C:16](Cl)(=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:9])=[C:6]([NH:7][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 72652-Amino-4-chlorophenolHCID 69819Nonanoyl chloride

Product 1

HCID 13255813HCID 13255813, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

5-Chloro-2-hydroxy aniline, 10.3 g (0.072 mole), is dissolved in 200 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at 70° C. while nonanoyl chloride is added slowly. The solution is stirred for 2 hours. Excess pyridine is removed by washing the product with 4N hydrochloric acid. The product is then passed through a florisil column and crystallized at -20°. There is obtained N-(5-chloro-2-hydroxyphenyl) nonanamide (M.P. 93.5-94.0). Analysis shows 4.94% nitrogen and 12.53% chlorine as against calculated values of 49.4% and 12.49% respectively, for C15H22ClNO2.

Workup

  1. additionis added slowly
  2. customExcess pyridine is removed
  3. washby washing the product with 4N hydrochloric acid
  4. customcrystallized at -20°

Sources & evidence

ORD record
ord-460312e64ac34fd997d96ee284eb3aed
Source dataset
uspto-grants-1987_05
Patent number
US04663353

Reaction notes

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