3-Cyanopyridine → Nicotinamide

HRID 1181169Notes

Reaction equation

HRID 1181169 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:10].C(#[N:19])C.[OH2:20].CN(C)[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=C[CH:25]=1>C(#N)C>[C:9]([NH2:10])(=[O:30])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.[C:23]([OH:30])(=[O:20])[C:24]1[CH:29]=[CH:28][CH:27]=[N:19][CH:25]=1

Participants

7

Reactant 4

HCID 793-Cyanopyridine3×HCID 11916N,N-DimethylbenzamideHCID 62657Potassium Phosphate, TribasicHCID 18373917Acetonitrile--water (1/1)

Product 2

HCID 936NicotinamideHCID 938Nicotinic Acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 15-mL polypropylene centrifuge tube was added 3.73 mL of 50 mM potassium phosphate buffer (pH 7.0), 1.0 mL of an E. coli SW132 cell extract suspension prepared as described above, and 0.2626 g of 3-cyanopyridine. The final concentration of 3-cyanopyridine was 0.494 M. The reaction mixture was mixed on a rotating platform at 23° C. After 15 min, 7.50 mL of 95:5 acetonitrile/water containing 0.30 M N,N-dimethylbenzamide (HPLC external standard) was added to the reaction, the resulting mixture centrifuged, and a 0.100 mL of the supernatant mixed with 0.900 mL of acetonitrile and analyzed by HPLC. The conversion of 3-cyanopyridine was 100%, and the yields of nicotinamide and nicotinic acid were 100% and 0%, respectively.

Workup

  1. extractioncell extract suspension
  2. customprepared
  3. additionThe reaction mixture was mixed on a rotating platform at 23° C

Sources & evidence

ORD record
ord-08c41c0c001742c49613d59c304765df
Source dataset
uspto-grants-2007_10
Patent number
US07285406B2

Reaction notes

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