Methyl 3-methylquinoline-2-carboxylate → cis-2-Methoxycarbonyl-3-methyltetrahydroquinoline

HRID 52515Notes

Reaction equation

HRID 52515 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([CH3:15])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[H][H]>C(O)(=O)C.[Pt]=O>[CH3:1][O:2][C:3]([C@H:5]1[C@@H:14]([CH3:15])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)=[O:4]

Participants

5

Reactant 2

HCID 10954600Methyl 3-methylquinoline-2-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67722227cis-2-Methoxycarbonyl-3-methyltetrahydroquinolineYield 78.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

2-Methoxycarbonyl-3-methylquinoline (30 g, 0.149 mol) in acetic acid (300 mL) was hydrogenated over platinum oxide (1 g) under atmospheric pressure of hydrogen at room temperature until the theoretical amount of hydrogen was consumed. The mixture was passed through celite and concentrated in vacuo. The residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate to give 23.93 g of cis-2-methoxycarbonyl-3-methyltetrahydroquinoline (78%): 1H NMR (270 MHz, CDCl3) d 6.99 (m, 2H), 6.64 (t, 1H, J=7.9 Hz), 6.58 (d, 1H, J=7.9 Hz), 4.34 (s, 1H), 4.09 (t, 1H, J=2.5 Hz), 3.06 (dd, 1H, J =16.9, 5.8 Hz), 2.55 (m, 1H), 2.50 (dd, 1H, J=16.9, 3.3 Hz), 0.88 (d, 3H, J=6.9 Hz).

Workup

  1. customwas consumed
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-8a325ff51eb34f1288698858a330fe44
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…