Ethanol → 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol

HRID 326047Notes

Reaction equation

HRID 326047 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.S([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1)(O)(=O)=O.C(O)C>O>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:24]([C:21]1[CH:22]=[CH:23][C:18]([OH:17])=[CH:19][CH:20]=1)[CH3:25])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 702EthanolHCID 6075022,6-DichloroquinolineHCID 10198132p-(N-methylamino)phenol sulfate

Product 1

HCID 204619604-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2,6-dichloroquinoline (1.1 g; prepared according to the method of O Fischer, Chem. Ber., 35, 3683 (1902), 4-(N-methylamino)phenol sulfate (1.5 g), ethanol (5 ml) and water (20 ml) was heated under reflux for a period of 24 hours. Water (50 ml) was added to the mixture and the aqueous mixture was extracted with chloroform (2×100 ml). The chloroform extracts were dried (anhydrous MgSO4) and the solvent was evaporated to give 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol (1.1 g) as a dark oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 8.0-6.6 and 7.2 (10H, m and d of d, quinoline, hydroxy and phenyl protons); 3.6 (3H, s, N--CH3).

Workup

  1. customprepared
  2. temperatureunder reflux for a period of 24 hours
  3. extractionthe aqueous mixture was extracted with chloroform (2×100 ml)
  4. dry with materialThe chloroform extracts were dried (anhydrous MgSO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-37489c974622447eb1ccd989ce18ad71
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

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