Lithium Hydroxide → HCID 18931452, compound

HRID 1598976Notes

Reaction equation

HRID 1598976 reaction equation
[CH3:1][C:2]1([CH3:33])[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)[C:4](=[O:32])[CH2:3]1.[Li+].[OH-]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:33])[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][C:28]([CH3:31])=[CH:27][CH:26]=2)[C:4](=[O:32])[CH2:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18931449HCID 18931449, compound2×

Product 1

HCID 18931452HCID 18931452, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.080 g (0.18 mmol) of ethyl 4-(2-(4,4-dimethyl-3,4-dihydro-N-(4-methylphenyl)-2(1H)-quinolinon-7-yl)ethynyl)benzoate (Compound 21) in 4.0 mL of tetrahydrofuran and 1.0 mL of methanol was added 1.0 mL (1.3 mmol) of 1.3M aqueous LiOH. The resulting solution was heated at 50° C. for 5 hours. The mixture was concentrated in vacuo, water was added, and the mixture was extracted with ether (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude product was purified by recrystallization from acetonitrile to give the title compound as a yellow solid. PNMR (500 MHz, DMSO) d 1.31 (6 H, s), 2.35 (3 H, s), 2.59 (2 H, s), 6.32 (1 H, d, J=7.1 Hz), 7.10 (1 H, d, J=8.3 Hz), 7.23 (1 H, dd, J=8.1, 1.7 Hz), 7.32 (1 H, d, J=8.3 Hz), 7.42 (1 H, d, J=8.1 Hz), 7.51 (1 H, d, J=8.3 Hz), 7.84 (1 H, d, J=8.3 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with ether (2x)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-c7697a2149db4871aab88a8183c23430
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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