Phenol → HCID 13603928, compound

HRID 638294Notes

Reaction equation

HRID 638294 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl: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:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:3]=[C:2]2[N:20]1[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 13603902HCID 13603902, compound

Product 1

HCID 13603928HCID 13603928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.1 g of 4,6-dichloro-2-(4-chlorophenyl)quinoline, 2.56 g (20 mmol) of isonipecotamide, and 10 g of phenol was stirred and heated in an oil bath at 160°-170° for 4 hr. It was then cooled and diluted with water. It was 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 2.45 g of crude product. Recrystallization from ethanol gave the above-named compound as off-white prisms, mp 272°-275°.

Workup

  1. temperatureheated in an oil bath at 160°-170° for 4 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 2.45 g of crude product
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a00a9183c0164a74992f668e8c222c33
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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