6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

HRID 1766242Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2>CO.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

Conditions

Temperature: 40 °C

Procedure

6-Methoxyquinoline (48 g, 0.30 mol) was dissolved in 500 mL methanol and mix with PtO2 (12 g, 52.8 mmol), the mixture was put in a Parr shaker heated to 40° C. under hydrogen (40 psi (275 kPa)) for 24 h. The reaction was cool to room temperature, released the pressure, and then removed the catalyst. The solvent was concentrated resulting the title compound: 1H NMR (300 MHz, CDCl3) 1.90-1.97 (m, 2), 2.75 (t, 2H, J=6.4 Hz), 3.25 (t, 2H, J=5.5 Hz), 3.72 (s, 3H), 6.44-6.60 (m, 3H). cl PREPARATION 36

Workup

temperatureThe reaction was cool to room temperature
customremoved the catalyst
concentrationThe solvent was concentrated

Sources & evidence

ORD record: ord-68239fc616bf4e349dace0bc61e3c043
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230011B2

Reaction notes

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