Phenol → HCID 13603931, compound

HRID 638300Notes

Reaction equation

HRID 638300 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]([F: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>[F: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 13603903HCID 13603903, compound

Product 1

HCID 13603931HCID 13603931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of 4-chloro-2-(4-fluorophenyl)-6-methylquinoline, 1.88 g (10 mmol) of isonipecotamide, and 4 g of phenol was stirred and heated in an oil bath at 165°-170° for 2 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 1.9 g of crude product, mp 264°-271° dec. Recrystallization from pyridine gave the titled product as off-white prisms, mp 275°-277° dec.

Workup

  1. temperatureheated in an oil bath at 165°-170° for 2 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 1.9 g of crude product, mp 264°-271° dec
  8. customRecrystallization from pyridine

Sources & evidence

ORD record
ord-8a720415c2264d1781ac106c76d8a96e
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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