N-Phenyl-p-phenylenediamine → N-(4-anilinophenyl)-2-hydroxyisobutyramide

HRID 895050Notes

Reaction equation

HRID 895050 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[OH:15][C:16]([CH3:21])([CH3:20])[C:17](O)=[O:18]>>[NH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:17](=[O:18])[C:16]([OH:15])([CH3:21])[CH3:20])=[CH:10][CH:9]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7564N-Phenyl-p-phenylenediamineHCID 116712-Hydroxyisobutyric acid

Product 1

HCID 20574123N-(4-anilinophenyl)-2-hydroxyisobutyramideYield 89%

Conditions

Temperature
250 °C

Procedure

A 100 milliliter flask was charged with 18.4 grams (0.10 mole) p-aminodiphenylamine and 10.6 grams (0.102 mole) α-hydroxy isobutyric acid from Example 1. The mixture was heated to 190° C. where dehydration of the amine-acid salt begins. Water was distilled from the mixture as the temperature slowly increased to 250° C. 2.35 milliliters of distillate was collected and the color of the mixture turned from blue-black to clear amber. After cooling the mixture to 190° C., the amber liquid was poured into a crystallizing dish whereupon it immediately crystallized to give 24.0 gram of N-(4-anilinophenyl)-2-hydroxy-isobutyramide (89% yield).

Workup

  1. distillationWater was distilled from the mixture as the temperature
  2. distillation2.35 milliliters of distillate was collected
  3. temperatureAfter cooling the mixture to 190° C.
  4. additionthe amber liquid was poured into a crystallizing dish whereupon it
  5. customimmediately crystallized

Sources & evidence

ORD record
ord-0979dff5e9c24e58a725a10df8960927
Source dataset
uspto-grants-1981_08
Patent number
US04286105

Reaction notes

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