Sodium borohydride → 2-Cyano-5-hydroxymethylpyridine

HRID 8909Notes

Reaction equation

HRID 8909 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[N:7][CH:6]=1)C.[BH4-].[Na+]>CO>[OH:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([C:11]#[N:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13415155Ethyl 6-cyanonicotinate

Product 1

HCID 122519662-Cyano-5-hydroxymethylpyridineYield 34.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl-6-cyanonicotinate (prepared as per T. Sakamoto, S. Kaneda, S. Nishimura and H. Yamanaka Chem. Pharm. Bull. 1985, 33, 565) (1.58 g, 8.97 mmol) in MeOH (40 mL) was added NaBH4 (1.00 g, 26.4 mmol) and the reaction stirred at room temperature for 8 h. After removal of the solvent, the residue was taken up in 15% NaOH (5 mL) and stirred for 20 min. The mixture was then extracted repeatedly with CH2Cl2, and the combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (EtOAc/hexanes, 1:1) afforded 3-hydroxymethyl-6-cyanopyridine (414 mg, 34%). 1H NMR (CDCl3) δ 5.16 (s, 2H), 7.69 (d, 1H, J=6.8 Hz), 7.84 (d, 1H, J=6.8 Hz), 8.71 (s, 1H).

Workup

  1. customAfter removal of the solvent
  2. stirringstirred for 20 min
  3. extractionThe mixture was then extracted repeatedly with CH2Cl2
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by chromatography on silica gel (EtOAc/hexanes, 1:1)

Sources & evidence

ORD record
ord-ca0cab19f1de48d68d061e1415cf7894
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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