Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate → 6-Methoxy-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline

HRID 495467Notes

Reaction equation

HRID 495467 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][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2Cl.CCOC(C)=O.CC(O)=O.[H][H]>CO.[Pt]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6]2

Participants

6

Reactant 3

HCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylateHCID 22609514Ethyl acetate acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 223268186-Methoxy-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 6-methoxy-4-chloro-3-ethoxycarbonyl-quinoline (Step B, 20 g, 0.075 mol) in 1/1 EtOAc/AcOH (560 mL) in a Parr hydrogenation apparatus bottle kept under inert atmosphere was added Pt/C 10% (2 g). The mixture was hydrogenated under 60 psi hydrogen at RT for 2 h using a Parr hydrogenation apparatus. The resulting mixture was diluted with MeOH and filtered. The solid was washed several times with a 1/1 MeOH/CH2Cl2 mixture and the solvents were removed under vacuum. The resulting solid was suspended into CH2Cl2 and 2N NaOH was added. The mixture was stirred at RT for 30 min. The organic layer was recovered and washed once with 2 N NaOH and twice with water to give crude 6-methoxy-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline, which was directly used in the next step.

Workup

  1. filtrationfiltered
  2. washThe solid was washed several times with a 1/1 MeOH/CH2Cl2 mixture
  3. customthe solvents were removed under vacuum
  4. additionwas added
  5. customThe organic layer was recovered
  6. washwashed once with 2 N NaOH and twice with water

Sources & evidence

ORD record
ord-3ef58c1832b64c518615020d6abd41db
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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