3-Cyanopyridine → Nicotinamide

HRID 750439Notes

Reaction equation

HRID 750439 reaction equation
C(#[N:3])C.[OH2:4].C[N:6](C)[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=C[CH:9]=1.[C:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)#N>C(#N)C>[C:7]([NH2:6])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[N:3][CH:9]=1.[C:16]([OH:14])(=[O:4])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1

Participants

6

Reactant 3

HCID 793-CyanopyridineHCID 11916N,N-DimethylbenzamideHCID 18373917Acetonitrile--water (1/1)

Product 2

HCID 936NicotinamideHCID 938Nicotinic Acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At the completion of the reaction (100% conversion of nitrile), the product mixture was decanted from the biocatalyst beads, and 0.2 mL of 0.20 M calcium acetate buffer (pH 7.0, 2.0 mM final calcium ion concentration in reaction mixture), 16.56 mL of distilled, deionized water, and 2.127 g of 3-cyanopyridine was added to the catalyst beads in the reaction vessel. The final concentration of 3-cyanopyridine was 1.06 M in 20 mL of reaction mixture. Samples (0.100 mL) of the reaction mixture were mixed with 0.400 mL of 95:5 acetonitrile/water containing 0.30 M N,N-dimethylbenzamide (HPLC external standard), and a 0.100 mL of the resulting solution mixed with 0.900 mL of acetonitrile and analyzed by HPLC. After 23 h, the conversion of 3-cyanopyridine was 100%, and the yields of nicotinamide and nicotinic acid were 100% and 0%, respectively. The initial reaction rate for production of nicotinamide, measured during the first 30 min of reaction, was 4.60 mM/minute.

Workup

  1. customthe product mixture was decanted from the biocatalyst beads, and 0.2 mL of 0.20 M calcium acetate buffer (pH 7.0, 2.0 mM final calcium ion concentration in reaction mixture), 16.56 mL
  2. distillationof distilled
  3. additiondeionized water, and 2.127 g of 3-cyanopyridine was added to the catalyst beads in the reaction vessel
  4. customin 20 mL of reaction mixture

Sources & evidence

ORD record
ord-5a630ca4120b4d7fa4ed3183819dbf17
Source dataset
uspto-grants-2008_07
Patent number
US07405064B2

Reaction notes

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