Hydrochloric Acid → HCID 67856644, compound

HRID 484429Notes

Reaction equation

HRID 484429 reaction equation
[NH2:1][C:2]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:15])=[CH:11][C:12]=2[Cl:14])[NH:7][C@@H:6]([C:16]([O:18]C)=[O:17])[CH2:5]1)=[O:3].[OH-].[Na+].Cl>CO.O>[NH2:1][C:2]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:15])=[CH:11][C:12]=2[Cl:14])[NH:7][C@@H:6]([C:16]([OH:18])=[O:17])[CH2:5]1)=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67856643HCID 67856643, compound

Product 1

HCID 67856644HCID 67856644, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Cis-4-aminocarbonyl-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.12 g) was dissolved in 50% aqueous methanol (20 ml) and 1N sodium hydroxide solution (0.6 ml) was added. The reaction mixture was stirred at room temperature for 14 h then the solvents were evaporated in vacuo to leave a residue which was redissolved in water (20 ml) and acidified to pH 1 with concentrated hydrochloric acid. The aqueous solution was extracted with ethyl acetate (3×40 ml), dried (Na2SO4), filtered and concentrated under vacuum to give an off white solid which was triturated with diethyl ether and collected by filtration to give the title compound (0.082 g, m.p. 220°-222° C.); δ (360 MHz, DMSO) 2.28 (2H, m, CHACHBHCCHD), 3.71 (1H, m, CHACHBHCCHD), 3.89 (1H, m, CHACHBHCCHD), 6.62 (1 H, d, J=2.1 Hz, 6-H or 8-H), 6.64 (1H, br, s, NH), 6.74 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.81 (1H, s, br, NH), 7.26 (1H, s, br, NH); m/e (FAB) 289 (M+1); Found: C, 44.84; H, 3.67; N, 8.95. C11H10Cl2N2O3.0.4H2O requires C, 44.59; H, 3.67; N, 9.45%.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customto leave a residue which
  3. extractionThe aqueous solution was extracted with ethyl acetate (3×40 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give an off white solid which
  8. customwas triturated with diethyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c7af220fb7e24224a976f4e969f7aeff
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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