Lithium hydroxide, monohydrate → HCID 71284456, compound

HRID 1481682Notes

Reaction equation

HRID 1481682 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:21]([O:23]C)=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH2:14][CH2:13][CH2:12]2)[CH3:2].O[Li].O>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[C:5]([C:21]([OH:23])=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH2:14][CH2:13][CH2:12]2)[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71284791HCID 71284791, compound

Product 1

HCID 71284456HCID 71284456, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of methyl 5-ethyl-6-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (200 mg, 0.61 mmol) in THF (1 mL) and H2O (1 mL) was added LiOH—H2O (85 mg, 2.03 mmol, 3.3 eq) at room temperature. The reaction mixture was heated to 65° C. and stirred for 1 h. The reaction was monitored by LC-MS. Upon complete consumption of starting material, the reaction was quenched with 1N HCl (2 mL). The precipitate was collected by filtration then washed with Et2O to afford the title compound as a yellow solid (121 mg, 0.39 mmol, 14% over three steps).

Workup

  1. customUpon complete consumption of starting material
  2. customthe reaction was quenched with 1N HCl (2 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washthen washed with Et2O

Sources & evidence

ORD record
ord-4f1afa430bdd4f8c9e28be484b172f05
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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