Lithium Hydroxide → HCID 15168509, compound

HRID 484434Notes

Reaction equation

HRID 484434 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(CCC)=O)[CH2:5][C@H:6]([C:14]([O:16]C)=[O:15])[N:7]2N.[OH-:23].[Li+]>O1CCCC1.O>[C:14]([C@H:6]1[CH2:5][C@H:4]([NH:7][C:6]([CH2:5][CH2:4][CH3:3])=[O:23])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67690931HCID 67690931, compound

Product 1

HCID 15168509HCID 15168509, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-5,7-dichloro-2-methoxycarbonyl-4-n-propylcarbonyl-amino-1,2,3,4-tetrahydroquinoline (0.70 g, 0.493 mmol) in a mixture of tetrahydrofuran (15 ml) and water (5 ml) was added aqueous lithium hydroxide (1.1 ml of a 0.50M solution, 0.55 mmol) and the resulting mixture was stirred at room temperature for 20 h. The organic solvent was then removed under vacuum and the aqueous residue was diluted with dilute sodium bicarbonate solution (50 ml) then washed with ethyl acetate (1×30 ml). The aqueous phase was separated, acidified with dilute hydrochloric acid and extracted with ethylacetate (2×50 ml). The combined extracts were washed with brine (1×50 ml), dried (MgSO4) and evaporated to give a solid which was triturated with diethyl ether to give the title compound as colourless crystals (0.123 g) m.p. 174°-176° C. (dec). δ (DMSO, 360 MHz) δ 0.85 (3H, t, J=7.4 Hz, COCH2CH2CH3), 1.48-1.64 (3H, m, CHACHBHCCHD) and COCH2CH2CH3), 2.04 (2H, t, J=7.2 Hz, COCH2CH2CH3), 2.16 (1H, dm, J=13.1 Hz, CHACHBHCCHD), 3.82 (1H, dd, J=12.6 and 2.8 Hz, CHACHBHCCHD), 5.01 (1H, m, CHACHBHcCHDNHCO) 6.64 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.76 (1H, s, ArNH), 6.87 (1H, d, J=2.1 Hz, 6-H or 8-H), 8.10 (1H, d, J=7.2 Hz, --CHDNHCO--); m/e 330 (M+), 198 (100%, M-NHCOCH2CH2CH3, CO2H and H); Found C, 50.09; H, 4.78; N, 8.41; C14H16Cl2N2 03.0.2H2O requires C, 50.22; H, 4.94; N, 8.37%.

Workup

  1. customThe organic solvent was then removed under vacuum
  2. additionthe aqueous residue was diluted with dilute sodium bicarbonate solution (50 ml)
  3. washthen washed with ethyl acetate (1×30 ml)
  4. customThe aqueous phase was separated
  5. extractionextracted with ethylacetate (2×50 ml)
  6. washThe combined extracts were washed with brine (1×50 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a solid which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-e14c17f575af4fccb88f34b9104e7a57
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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