Lithium Hydroxide → 6-(Hydroxymethyl)pyridine-3-carbonitrile

HRID 639149Notes

Reaction equation

HRID 639149 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10]C(=O)C)=[N:7][CH:8]=1)#[N:2].[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C>[OH:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67557567(5-Cyano-2-pyridinyl)methylacetate

Product 1

HCID 534276876-(Hydroxymethyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 31A (180 mg, 1.02 mmol) is dissolved in tetrahydrofuran (8 ml). Lithium hydroxide (48.94 mg, 2.04 mmol) is dissolved in water (5 ml) and added to the THF solution. The reaction is stirred for 2 hours at room temperature. The mixture is diluted with water and ethyl acetate. The aqueous phase is extracted three times with ethyl acetate. The organic phases are combined and washed with brine, dried with magnesium sulphate monohydrate, filtered and concentrated in vacuo. The residue is used without further purification.

Workup

  1. extractionThe aqueous phase is extracted three times with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried with magnesium sulphate monohydrate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is used without further purification

Sources & evidence

ORD record
ord-af485c9f42dd4999a4a725ef0f71d73b
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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