1-Butanol → 4-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

HRID 1720273Notes

Reaction equation

HRID 1720273 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH2:14](N)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(O)CCC.Cl>CO>[OH2:12].[ClH:1].[CH2:27]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 16217TetradecylamineHCID 7715204-Chloro-2-methylquinolin-6-ol

Product 1

HCID 224179544-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 150 mg (0.78 mmol) of 4-chloro-2-methylquinolin-6-ol, 174 mg (0.81 mmol) of n-tetradecylamine, and 5 mL of n-butanol was heated under reflux for 24 hours. Excess butanol was removed by codistillation with cyclohexane. The residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane) to furnish crude product. This was taken up in methanol, and the solution was treated with dry hydrogen chloride gas. The solution was evaporated under reduced pressure to give the title compound as crystalline material: m.p. 180°-183° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customExcess butanol was removed by codistillation with cyclohexane
  3. customThe residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane)
  4. customto furnish crude product
  5. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-340b3e54260d4e0587106922691e4d8e
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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