Sulfuric Acid → 4-(Hydroxymethyl)pyridine-2-carbonitrile

HRID 2202590Notes

Reaction equation

HRID 2202590 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]#[N:17])[CH:11]=1)(C(C)(C)C)(C)C.S(=O)(=O)(O)O>C(O)C>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]#[N:17])[CH:11]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 145414484-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

Product 1

HCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrileYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol, 4-(tert-butyldimethylsilyloxymethyl)pyridine-2-carbonitrile (260 mg, 1.1 mmol) synthesized in Production Example 86 was dissolved, and concentrated sulfuric acid (123 μL, 2.3 mmol) was added thereto. The mixture was refluxed overnight. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature, and the solvent was distilled off. The resulting residue was dissolved in ethyl acetate and washed with water and a saturated saline solution in order. Thereafter, the organic layer was dried over magnesium sulfate, and the solvent was distilled off. Thus the title compound (111 mg, 78.8%) was obtained as a yellowish white solid.

Workup

  1. dissolutionwas dissolved
  2. temperatureThe mixture was refluxed overnight
  3. distillationthe solvent was distilled off
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThereafter, the organic layer was dried over magnesium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-1add06800e3d4d15ab6cc5487bcbd640
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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