Phenol → HCID 13603915, compound

HRID 638271Notes

Reaction equation

HRID 638271 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:3]=1.[NH:19]1[CH2:27][CH2:26][CH:22]([C:23]([NH2:25])=[O:24])[CH2:21][CH2:20]1.C1(O)C=CC=CC=1>O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[CH:3]=[C:2]([N:19]3[CH2:27][CH2:26][CH:22]([C:23]([NH2:25])=[O:24])[CH2:21][CH2:20]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 11832083HCID 11832083, compound

Product 1

HCID 13603915HCID 13603915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.44 g of 4-chloro-2-(4-fluorophenyl)quinoline 1.3 g (10 mmol) of isonipecotamide, and 3 g of phenol was stirred and heated in an oil bath at 165°-170° for 4.5 hr. It was then cooled and diluted with water. It wa made alkaline with 3N sodium hydroxide, and crystallization was induced by the addition of ether and scratching. The solid was collected and washed with ether to give 1.6 g of crude product. Recrystallization from ethanol/water gave white needles (0.42g). mp 218°-220° dec.

Workup

  1. temperatureheated in an oil bath at 165°-170° for 4.5 hr
  2. temperatureIt was then cooled
  3. customwith 3N sodium hydroxide, and crystallization
  4. additionwas induced by the addition of ether
  5. customThe solid was collected
  6. washwashed with ether
  7. customto give 1.6 g of crude product
  8. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-107e64fbe2a14a65a56cbb0958122f2e
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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