HCID 19747375, compound → HCID 67856769, compound

HRID 484423Notes

Reaction equation

HRID 484423 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([Cl:19])=[CH:9][C:10]=2[Cl:18])[N:5]=1)([OH:3])=[O:2].[H][H]>CO.[Pt]=O>[C:1]([C@H:4]1[CH2:13][C@@H:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([Cl:19])=[CH:9][C:10]=2[Cl:18])[NH:5]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 19747375HCID 19747375, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67856769HCID 67856769, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

2-Carboxy-5,7-dichloro-4-methoxycarbonylquinoline (4.8 g) was dissolved in methanol (300 ml) and platinum oxide (0.48 g) was suspended in the solution. Rapid stirring under one atmosphere of hydrogen at room temperature for 75 minutes, followed by filtration and evaporation gave a crude product which was purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent to give the title compound as a colourless solid (1.3 g, m.p. 154°-156° C.); δ (360 MHz, DMSO) 2.23 (1H, ddd, J=13.9, 7.1 and 5.3 Hz, CHACHBHCCHD), 2.66 (1H, dt, J=13.9 and 4.0 Hz, CHACHBHCCHD), 3.57 (3H, s, CH3), 3.86 (1H, dd, J=7.1 and 4.0 Hz, CHACHBHCCHD), 3.91 (1H, broad multiplet, CHACHBHCCHD), 5.74 (1H, broad s, NH), 6.56 (1H, d, J=1.9 Hz, 6-H or 8-H), 6.58 (1H, d, J=1.9 Hz, 6-H or 8-H); m/e 303 (M+) 198 (100%, M-H, CO2H and CO2Me); Found: C, 47.62; H, 3.60; N, 4.66. C12H11Cl2NO4 requires C, 47.39; H, 3.65; N, 4.61%.

Workup

  1. filtrationfollowed by filtration and evaporation
  2. customgave a crude product which
  3. customwas purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent

Sources & evidence

ORD record
ord-42bf4cf803244bffa9952c8f01820fa4
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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