Phenol → HCID 13603933, compound

HRID 638303Notes

Reaction equation

HRID 638303 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH:3]=1.[NH:20]1[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]1.C1(O)C=CC=CC=1>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[CH:3]=[C:2]([N:20]3[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 13603905HCID 13603905, compound

Product 1

HCID 13603933HCID 13603933, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g (35 mmol) of 4-chloro-2-(4-chlorophenyl)-6-methylquinoline, 8.9 g (70 mmol) of isonipecotamide, and 20 g of phenol was stirred and heated in an oil bath at 165°-170° for 3.5 hr. It was then cooled and diluted with water. Crystallization was induced by the addition of ethanol and scratching. The solid was collected and washed with ether to give 11.9 g of crude product. Recrystallization from pyridine gave the named compound as off-white prisms, mp 261°-265° dec.

Workup

  1. temperatureheated in an oil bath at 165°-170° for 3.5 hr
  2. temperatureIt was then cooled
  3. customCrystallization
  4. additionwas induced by the addition of ethanol
  5. customThe solid was collected
  6. washwashed with ether
  7. customto give 11.9 g of crude product
  8. customRecrystallization from pyridine

Sources & evidence

ORD record
ord-fc67790881d743d5b674dd996cec6daf
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

Loading…