Lithium Hydroxide → HCID 58188222, compound

HRID 1845331Notes

Reaction equation

HRID 1845331 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:18]([O:20]C)=[O:19])[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:10]=1)[CH3:3].[OH-].[Li+].[NH4+].[Cl-]>O1CCOCC1.O>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:18]([OH:20])=[O:19])[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:10]=1)[CH3:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 58188153HCID 58188153, compound

Product 1

HCID 58188222HCID 58188222, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 5-((dimethylamino)methyl)-4′-methylbiphenyl-3-carboxylate (90 mg, 0.32 mmol) in 1,4-dioxane (1.5 mL) and water (1.5 mL) was added lithium hydroxide (20 mg, 0.83 mmol). The reaction mixture was stirred at room temperature for 2 h, and then treated with aq. NH4Cl and extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography to afford the title compound. 1H NMR (CD3OD, 400 MHz): 8.29 (s, 1H), 7.79 (s, 1H), 7.60 (s, 1H), 7.59 (d, J=8.0 Hz, 2H), 7.28 (d, J=8.0 Hz, 2H), 4.27 (s, 2H), 2.81 (s, 6H), 2.38 (s, 3H).

Workup

  1. extractionextracted with EtOAc (15 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-20db32275df3472c96a8c7208c732e0c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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