Lithium Hydroxide → HCID 18931463, compound

HRID 1598967Notes

Reaction equation

HRID 1598967 reaction equation
[CH3:1][C:2]1([CH3:31])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][CH2:3]1.[Li+].[OH-]>O1CCCC1>[CH3:1][C:2]1([CH3:31])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18931445HCID 18931445, compound2×

Product 1

HCID 18931463HCID 18931463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.7 mg (0.02 mmol) of ethyl 4-(2-(4,4-dimethyl-1,2,3,4-tetrahydro-N-phenylquinolin-7-yl)ethynyl)benzoate (Compound 9) in 1.0 mL in tetrahydrofuran was added 0.5 mL (0.1 mmol) of 0.2M aqueous LiOH. The resulting solution was stirred at room temperature for 20 hours. The mixture was then concentrated in vacuo. Water was added, and the mixture was extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound as a yellow solid. PNMR (300 MHz, DMSO) d 1.31 (6 H, s), 1.81 (2 H, t, J=5.9 Hz), 3.58 (2 H, t, J=5.9 Hz), 6.61 (1 H, s), 6.87 (1 H, d, J=8.0 Hz), 7.19 (1 H, t, J=7.1 Hz), 7.26-7.33(3 H, m), 7.43 (2 H, t, J=7.1 Hz), 7.55 (2 H, d, J=8.2 Hz), 7.89 (2 H, d, J=8.2 Hz).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate (2x)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-915dd46386c84ea8b92aec5d88937eb0
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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