Hydrochloric Acid → HCID 66930099, compound

HRID 2261225Notes

Reaction equation

HRID 2261225 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[Li+].[OH-].Cl>O1CCOCC1.O>[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66930005HCID 66930005, compound

Product 1

HCID 66930099HCID 66930099, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(6-cyano-3-pyridinyl)benzoate (D8) (0.5 g) in dioxane (30 ml) was treated with 1.1 eq aqueous LiOH solution (2.3 ml), 1N) and stirred at rt for 2 days. Solvent was removed by evaporation to give a white solid which was dissolved in water (10 ml) and acidified with 2N HCl to give a white solid which was filtered and dried to give the title compound (D9) (0.35 g). LCMS electrospray (+ve) 224 (MH+).

Workup

  1. customSolvent was removed by evaporation
  2. customto give a white solid which
  3. customto give a white solid which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-276e6cf1990c4d0aad986f53a55f495f
Source dataset
uspto-grants-2010_12
Patent number
US07846922B2

Reaction notes

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