Sodium Hydroxide → HCID 44301326, compound

HRID 484424Notes

Reaction equation

HRID 484424 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([C:17]([O:19][CH3:20])=[O:18])[CH2:5][C@H:6]([C:13]([O:15]C)=[O:14])[NH:7]2.[OH-].[Na+]>CO>[C:13]([C@H:6]1[CH2:5][C@H:4]([C:17]([O:19][CH3:20])=[O:18])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15168462HCID 15168462, compound

Product 1

HCID 44301326HCID 44301326, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trans-5,7-dichloro-2,4-dimethoxycarbonyl-1,2,3,4-tetrahydroquinoline (1.13 g) was dissolved in 50% aqueous methanol (80 ml) and sodium hydroxide (0.16 g 1.1 molar equivalents) was added. The solution was stirred at room temperature for 4 h then concentrated in vacuo and redissolved in water (40 ml). The aqueous solution was washed with diethyl ether (2×20 ml) then acidified to pH 1 with 1N hydrochloric acid and extracted into diethyl ether (2×50 ml), dried (Na2SO4), filtered and the solvent evaporated to give an oil. This was purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent to give, as a colourless solid, trans-2-carboxy-5,7-dichloro-4-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.85 g, m.p. 160° C. dec); δ (360 MHz, DMSO), 1.91 (1H, ddd, J=13.4, 11.7 and 6.0 Hz, CHACHBHCCHD), 2.41 (1H, dm, J=13.4 Hz, CHACHBHCCHD), 3.65 (3H, s, CH3), 3.79 (1H, dd, J=11.7 and 3.2 Hz, CHACHBHCCHD), 3.96 (1H, dd, J=6.0 and 2.5 Hz, CHACHBHCCHD), 6.66 (1H, d, J=2.1 Hz. 6-H or 8-H), 6.83 (1H, d, J=2.1 Hz, 6-H or 8-H); m/e 303 (M+) 198 (M-H, CO2H, CO2Me); Found: C, 47.31; H, 3.70; N. 4.57. C12H11Cl2NO4 requires C, 47.39; H, 3.65; N, 4.61%.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionredissolved in water (40 ml)
  3. washThe aqueous solution was washed with diethyl ether (2×20 ml)
  4. extractionextracted into diethyl ether (2×50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customto give an oil
  9. customThis was purified by chromatography on silica gel with 2.5% methanol, 0.5% acetic acid and 97% dichloromethane as eluent

Sources & evidence

ORD record
ord-9066e6ace3ff457683a989c0272ecad5
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

Loading…