Lithium Hydroxide → HCID 9886988, compound

HRID 1598962Notes

Reaction equation

HRID 1598962 reaction equation
[CH3:1][C:2]1([CH3:32])[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][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH2:4][CH2:3]1.CC1(C)C2C(=CC(C#CC3C=CC(C([O-])=O)=CC=3)=CC=2)N(C2C=CC(C)=CC=2)CC1.[Li+].[OH-]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:32])[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:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 18931456HCID 18931456, compoundHCID 18931464HCID 18931464, compound

Product 1

HCID 9886988HCID 9886988, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(2-(4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)quinolin-7-yl)ethynyl)benzoate (Compound 4) (0.105 g, 0.25 mmol) in 10.0 mL of tetrahydrofuran and 0.5 mL of methanol was added 1.0 mL (1.5 mmol) of 1.5M aqueous LiOH. The resulting solution was stirred at room temperature for 24 hours. The mixture was 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, which was recrystallized from 2:1 acetonitrile:ethyl acetate to give yellow needles. PNMR (300 MHz, DMSO) d 1.31 (6 H, s), 1.80 (2 H, t, J=5.9 Hz), 2.31 (3 H, s), 3.53 (2 H, t, J=5.9 Hz), 6.50 (1 H, d, J=1.6 Hz), 6.83 (1 H, dd, J=8.0, 1.6 Hz), 7.16 (2 H, d, J=8.4 Hz), 7.25 (2 H, J=8.4 Hz), 7.29 (1 H, d, J=8.0 Hz), 7.55 (2 H, d, J=8.4 Hz), 7.89 (2 H, d, J=8.4 Hz)

Workup

  1. concentrationThe mixture was concentrated in vacuo, water
  2. additionwas 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-784f331e151f474bba9d57637bbefcdd
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

Loading…