Pyrrolidine → [8-Methyl-2-(pyrrolidin-1-yl)quinolin-3-yl]methanol

HRID 1627506Notes

Reaction equation

HRID 1627506 reaction equation
Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>CCOC(C)=O>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:11]([CH2:12][OH:13])=[CH:10]2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 865104(2-Chloro-8-methylquinolin-3-yl)methanol

Product 1

HCID 66777627[8-Methyl-2-(pyrrolidin-1-yl)quinolin-3-yl]methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2-Chloro-8-methylquinolin-3-yl)methanol (200 mg, 0.97 mmol) and pyrrolidine (2 mL) were stirred in a sealed tube at 100° C. for 4 h. After cooling, the solution was diluted with EtOAc and washed with water and brine. The organic layer was dried (MgSO4), filtered and the solvent was removed in vacuo. Purification by column chromatography on silica, eluting with 20% EtOAc in isohexane, gave the title compound (206 mg, 88%). δH (CDCl3) 7.86 (1H, s), 7.46 (1H, d, J=8.01 Hz), 7.40 (1H, d, J=7.04 Hz), 7.13 (1H, t, J=7.50 Hz), 4.85 (2H, s), 3.72 (4H, t, J=6.36 Hz), 2.65 (3H, s), 2.12 (1H, s), 2.03-1.96 (4H, m).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by column chromatography on silica
  7. washeluting with 20% EtOAc in isohexane

Sources & evidence

ORD record
ord-bab2f63a6668458aa7844ae7a89d2f65
Source dataset
uspto-grants-2014_07
Patent number
US08785628B2

Reaction notes

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