Pyridine → N-(4-Nitrophenyl)nonanamide

HRID 978100Notes

Reaction equation

HRID 978100 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[C:17](Cl)(=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>ClC(Cl)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74754-NitroanilineHCID 69819Nonanoyl chloride

Product 1

HCID 4319205N-(4-Nitrophenyl)nonanamide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

p-Nitroaniline, 13.0 g (0.094 mole), is dissolved in 200 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at 50° C. while nonanoylchloride, 16.5 g (0.094 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 and crystallized at -20° C. There is obtained N-(4-nitrophenyl) nonanamide, (M.P. 76.0°-76.5°). Analysis shows 9.91% nitrogen as against a calculated value of 10.06% for C15H21N2O3.

Workup

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

Sources & evidence

ORD record
ord-ddc1996e9b83451aa03c3a110a4a6c9d
Source dataset
uspto-grants-1987_05
Patent number
US04663353

Reaction notes

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