Pyridine → HCID 3412495, compound

HRID 978102Notes

Reaction equation

HRID 978102 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N1C=CC=CC=1.[C:18](Cl)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>ClC(Cl)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 124774-Chloro-3-nitroanilineHCID 69819Nonanoyl chloride

Product 1

HCID 3412495HCID 3412495, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-chloro-3-nitroaniline, 10.1 g (0.058 mole), is dissolved in 100 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at room temperature while nonanoylchloride, 10.5 g (0.067 mole), 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. The product does not crystallize from dichloroethane which was removed. The product was crystallized from 80% ethanol. There is obtained N-(4-Chloro-3-nitrophenyl) nonanamide (M.P. 44.5-45.0). Analysis shows 8.9% nitrogen and 11.26% chlorine as against calculated values of 8.96% and 11.33% respectively for C15H21ClN2O3.

Workup

  1. additionis added slowly
  2. customExcess pyridine is removed
  3. washby washing the product with 4N hydrochloric acid
  4. customThe product does not crystallize from dichloroethane which
  5. customwas removed
  6. customThe product was crystallized from 80% ethanol

Sources & evidence

ORD record
ord-5689686333fd4742ba4d7771eed97af8
Source dataset
uspto-grants-1987_05
Patent number
US04663353

Reaction notes

Loading…