Morpholine → 2-(morpholin-4-yl)quinolin-8-ol

HRID 1777141Notes

Reaction equation

HRID 1777141 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2748782-Chloroquinolin-8-ol

Product 1

HCID 7467522-(morpholin-4-yl)quinolin-8-olYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 2-chloroquinolin-8-ol (1.7 g crude, 9.5 mmol) was added morpholine (5 mL). The mixture was heated at reflux for 16 hours. After cooling, the mixture was diluted with water (40 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was used directly for the next step. (1.6 g, Yield 80%). LCMS (m/z): 231.1 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9105d0151f74d1c88121655c9357202
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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