Pyridine → HCID 5099852, compound

HRID 978099Notes

Reaction equation

HRID 978099 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([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:5]=[C:6]([NH:7][C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74233-NitroanilineHCID 69819Nonanoyl chloride

Product 1

HCID 5099852HCID 5099852, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

m-Nitroaniline, 10.0 g (0.072 mole), is dissolved in 150 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at room temperature while nonanoyl chloride, 12.9 g (0.073 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-(3-nitrophenyl) nonanamide (M.P. 63.0°-63.5° C.). Analysis shows 9.88% 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-0cbe03364ea84bcc9a58d749813f9acf
Source dataset
uspto-grants-1987_05
Patent number
US04663353

Reaction notes

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