Phenol → HCID 19603260, compound

HRID 1604522Notes

Reaction equation

HRID 1604522 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].C1(O)C=CC=CC=1>CC(C)=O>[ClH:1].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 66053N,N-DimethylethylenediamineHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 19603260HCID 19603260, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-chloro-8-hydroxy-2-methylquinoline (500 mg), N,N-dimethylethylenediamine (341 mg) and phenol (486 mg) was heated at 125° C. for 18 hours. After cooling the reaction mixture, acetone (5 ml) was added thereto. The precipitates were collected by filtration and recrystallized from acetonitrile to give 4-(2-dimethylaminoethylamino)-8-hydroxy-2-methylquinoline hydrochloride (415 mg)) as brown crystals.

Workup

  1. additionwas added
  2. filtrationThe precipitates were collected by filtration
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-1062b682bf0e4e9db2aa1dae63a3126d
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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