Phenol → HCID 13603925, compound

HRID 638287Notes

Reaction equation

HRID 638287 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]([CH3:19])=[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.[I-].[Na+].[OH-].[NH4+]>O.[Cu].CCOCC.C(OCC)(=O)C>[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]([CH3:19])=[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

10

Reactant 5

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 5238Sodium IodideHCID 14923Ammonium HydroxideHCID 13603900HCID 13603900, compound

Product 1

HCID 13603925HCID 13603925, compound

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.02 g (7 mmol) of 4,6-dichloro-2-(4-methylphenyl)quinoline, 1.6 g (12 mmol) of isonipecotamide, 5 g of phenol, and small amounts of sodium iodide and copper powder were stirred and heated at 160° for 4 hr. The reaction mixture was then diluted to 50 ml with water and made alkaline by the addition of concentrated ammonium hydroxide. The addition of ethyl acetate and ether induced the crystallization of 2.7 g of crude damp product. mp 260°-265°. The above-named compound was obtained as white needles, mp 265°-267° dec on recrystallization from ethanol.

Workup

  1. temperatureheated at 160° for 4 hr
  2. customthe crystallization of 2.7 g of crude damp product
  3. customThe above-named compound was obtained as white needles, mp 265°-267° dec on recrystallization from ethanol

Sources & evidence

ORD record
ord-7134b4adf6724f2e9c9fd5ddb48ced0d
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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