Ammonium Chloride → HCID 66803790, compound

HRID 1818888Notes

Reaction equation

HRID 1818888 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[N:12].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C.C(OC(=O)C)C>[OH:2][CH2:3][CH2:4][C:5]1[C:6]([C:11]#[N:12])=[CH:7][N:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 53419517Methyl 2-(3-cyanopyridin-4-YL)acetate

Product 1

HCID 66803790HCID 66803790, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.58 g of (3-cyano-pyridine-4-yl)-acetic acid methyl ester was dissolved in 18 mL of ethanol and slowly added with 682 mg of sodium borohydride at −0° C. and stirred for about 2 hours. The above mixture was added with 3 mL of saturated solution of ammonium chloride, diluted with 200 mL ethylacetate. Then, the organic solvent layer was washed with water, and saturated solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The filtrate was concentreated under reduced pressure and a silica gel column chromatography was performed on the resulting residue by using a mixed eluant of methylene chloride and methanol, wherein methylene chloride and methanol are mixed in 50:1 volume ratio, and 1.02 g (74%) of 4-(2-hydroxy-ethyl)-nicotinonitrile was obtained in colorless oil.

Workup

  1. washThen, the organic solvent layer was washed with water, and saturated solution of sodium chloride
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. additionare mixed in 50:1 volume ratio

Sources & evidence

ORD record
ord-e195e815ab8a474591b683a2e21efdf7
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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