4-Nitroaniline → HCID 9844557, compound

HRID 1577078Notes

Reaction equation

HRID 1577078 reaction equation
[C:1]([C:12]1[CH:20]=[C:16]([C:17]([OH:19])=O)[C:15]([OH:21])=[CH:14][CH:13]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].P(Cl)(Cl)Cl.[N+:26]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)([O-:28])=[O:27]>ClC1C=CC=CC=1>[C:1]([C:12]1[CH:20]=[C:16]([C:17]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=2)=[O:19])[C:15]([OH:21])=[CH:14][CH:13]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 24387Phosphorus trichlorideHCID 9904144HCID 9904144, compound

Product 1

HCID 9844557HCID 9844557, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

In a 100 ml round-bottom flask fitted with a condenser and drying tube is placed 5-n-decanoylsalicylic acid (1.85 g., 6.7 mmoles), dry chlorobenzene (50 ml), and phosphorous trichloride (0.47 g., 3.4 mmoles). The mixture is then stirred by means of a magnetic stirring bar while the mixture is heated to 60° C. for three hours. The resulting solution is cooled to room temperature and 0.93 g. (6.7 mmoles) of p-nitroaniline is added. The mixture is then heated to 60° C. for three hours, with stirring, and then refluxed for 24 hours. The solvent is removed by vacuum vaporization and the residue is recrystallized from ethanol-water. The crystalline product is triturated with concentrated hydrochloric acid, collected and washed with water. Recrystallization from ethanol-water gives 0.64 grams of 5-n-decanoyl-4'-nitrosalicylanilide, mp 142°-143° C.

Workup

  1. customIn a 100 ml round-bottom flask fitted with a condenser
  2. customdrying tube
  3. temperatureThe resulting solution is cooled to room temperature
  4. temperatureThe mixture is then heated to 60° C. for three hours
  5. stirringwith stirring
  6. temperaturerefluxed for 24 hours
  7. customThe solvent is removed by vacuum vaporization
  8. customthe residue is recrystallized from ethanol-water
  9. customThe crystalline product is triturated with concentrated hydrochloric acid
  10. customcollected
  11. washwashed with water
  12. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-7710045bd7be4b4498739eff7c13cd23
Source dataset
uspto-grants-1981_09
Patent number
US04287191

Reaction notes

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