3-Cyanopyridine → 6-Hydroxynicotinonitrile

HRID 1648172Notes

Reaction equation

HRID 1648172 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[C:5]([C:7]1[CH:8]=[N:9]C=C[CH:12]=1)#[N:6]>>[C:8]([C:7]1[CH:5]=[N:6][C:1]([OH:4])=[CH:2][CH:12]=1)#[N:9]

Participants

3

Conditions

Temperature
30 °C

Procedure

To an Erlenmeyer flask equipped with navels was filled a nutrient solution containing 1 g of yeast extract, 1 g of glucose, 0.3 g of K2HPO4, 0.1 g of KH2PO4, 1 mg of FeSO4, 50 mg of MgSO4, 1 mg of MnSO4 and 100 ml of water, and the resultant mixture was sterilized at 120° C. for 20 minutes. After cooling to 30° C., the mixture was added with separately sterilized 1 mg of CuSO4 and 0.2 g of 3-cyanopyridine as an inducer. One of the microorganisms listed in Table 1 which was incubated on nutrient agar medium for 24 hours was inoculated into the above mixture with a platinum loop, and the mixture was incubated at 30° C. for 24 hours using a rotary shaker of 160 rpm. After 24 hours, the broth was recovered and centrifuged. The cells separated were suspended in and washed with 0.02 mol of an acetate buffer (pH 5.5) and centrifuged to give a resting cell. To a 100 ml reactor was added 20 ml of 1.0% 3-cyanopyridine (pH 5.5), and the mixture was heated at 30° C., and mixed with the resting cell obtained above. The resultant mixture was stirred sufficiently for 24 hours to give 3-cyano-6-hydroxypyridine. The product was identified by means of HPLC, IR and 1H-NMR. Table 1 shows the results.

Workup

  1. customTo an Erlenmeyer flask equipped with navels
  2. additionwas filled a nutrient solution
  3. additioncontaining 1 g of yeast
  4. extractionextract
  5. additionthe mixture was added with separately sterilized 1 mg of CuSO4 and 0.2 g of 3-cyanopyridine as an inducer
  6. waitwas incubated on nutrient agar medium for 24 hours
  7. waitthe mixture was incubated at 30° C. for 24 hours
  8. waitAfter 24 hours
  9. customthe broth was recovered
  10. customThe cells separated
  11. customto give a resting cell
  12. temperaturethe mixture was heated at 30° C.
  13. additionmixed with the resting cell
  14. customobtained above

Sources & evidence

ORD record
ord-90040f21890f43f9b93b4cb8a952e64b
Source dataset
uspto-grants-1995_07
Patent number
US05436145

Reaction notes

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