Lithium Hydroxide → HCID 69226247, compound

HRID 2113904Notes

Reaction equation

HRID 2113904 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[N:17][C:18]([N:21]([CH3:23])[CH3:22])=[CH:19][CH:20]=3)[N:11]=2)[CH:5]=1.[Li+].[OH-]>O1CCOCC1>[CH3:22][N:21]([CH3:23])[C:18]1[N:17]=[CH:16][C:15]([C:12]2[N:11]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])[O:14][N:13]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69222561HCID 69222561, compound

Product 1

HCID 69226247HCID 69226247, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 250 ml round flask, 7.0 g (21.6 mmol) of 3-[3-(6-dimethylamino-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-benzoic acid methyl ester is dissolved in 150 ml of dioxane and treated with 32.4 ml (1M, 32.4 mmol, 1.5 eq.) of aqueous LiOH solution. After 20 h, the solvent is removed under vacuo and the residue suspended in 300 ml H2O. The pH value is then adjusted to 2 by addition of 1M HCl-solution. The precipitate is stirred for 30 minutes, then filtered, washed with 0.1 M HCl-solution and with diethyl-ether and dried. This yields the title compound as light yellow solid. Mass spectrum: m/z (M+H)+: 311.0

Workup

  1. customthe solvent is removed under vacuo
  2. additionThe pH value is then adjusted to 2 by addition of 1M HCl-solution
  3. filtrationfiltered
  4. washwashed with 0.1 M HCl-solution and with diethyl-ether
  5. customdried

Sources & evidence

ORD record
ord-40ffbae258d949a5975eb9685c0cf10d
Source dataset
uspto-grants-2008_10
Patent number
US07432293B2

Reaction notes

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