2-Carboxy-5,7-dichloro-4-ethoxycarbonylquinoline → cis-2-Carboxy-5,7-dichloro-4-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline

HRID 484422Notes

Reaction equation

HRID 484422 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([Cl:20])=[CH:9][C:10]=2[Cl:19])[N:5]=1)([OH:3])=[O:2].[H][H]>C(O)C.[Pt]=O>[C:1]([C@H:4]1[CH2:13][C@@H:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([Cl:20])=[CH:9][C:10]=2[Cl:19])[NH:5]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 197475142-Carboxy-5,7-dichloro-4-ethoxycarbonylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 67856645cis-2-Carboxy-5,7-dichloro-4-ethoxycarbonyl-1,2,3,4-tetrahydroquinolineYield 55.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

2-Carboxy-5,7-dichloro-4-ethoxycarbonylquinoline (1.6 g) was dissolved in ethanol (100 ml) and platinum oxide (0.16 g) was suspended in the solution. The reaction mixture was stirred under one atmosphere pressure of hydrogen for 1 h at ambient temperature, then filtered and concentrated in vacuo. Chromatography on SiO2 with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane gave, as a colourless solid, cis-2-carboxy-5,7-dichloro-4-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.9 g, m.p. 160°-162° C.); δ (360 MHz, DMSO), 1.15 (3H, t, J=7.1 Hz, CH3CH2), 2.17 (1H, m, CHACHBHCCHD), 2.52 (1H, m, CHACHBHCCHD), 3.85 (1H, dd, J=7.1 and 3.1 Hz, CHACHBHCCHD), 3.98 (3H, m, CH3CH2 and CHACHBHCCHD), 6.65 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.87 (1H, br, s, NH); m/e 317 (M+), 198 (100%, M-CO2H, CO2Et and H); Found: C, 49.12; H, 4.18; N, 4.27. C13H13Cl2NO4 requires C, 49.08; H, 4.22; N. 4.40%.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e73d8e8f21b846e491be135cc2bdc45f
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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