4-Pyridinecarbaldehyde oxime → HCID 178526344, compound

HRID 1716175Notes

Reaction equation

HRID 1716175 reaction equation
Cl.NO.N1C=CC(C=[O:11])=CC=1.[N:12]1[CH:17]=[CH:16][C:15]([CH:18]=[N:19][OH:20])=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[OH:11][C:13]1[CH:14]=[C:15]([CH:18]=[N:19][OH:20])[CH:16]=[CH:17][N:12]=1

Participants

7

Reactant 5

HCID 127644-Pyridinecarbaldehyde oxime2×HCID 133894-PyridinecarboxaldehydeHCID 62657Potassium Phosphate, TribasicHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178526344HCID 178526344, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

1.3 g of hydroxylamine hydrochloride was solved to 5 g of ion-exchange water, and the solution was heated to 65° C. Then 2 g of 4-pyridinecarbaldehyde was added dropwise. The reaction was carried out at 65° C., for 30 minutes, and a solution containing 2.2 g of 4-pyridinaldoxime was obtained. The resulting 4-pyridinaldoxime was identified by HPLC analysis. Thereafter, the reaction solution was cooled to 30° C., and was neutralized by saturated sodium hydrogen carbonate solution to be adjusted to pH 6. Six hundred mL of 0.1 M potassium phosphate buffer (adjusted to pH 7.0) was added to the neutralized solution. Further, as in Example 1, the Delftia species YGK-A649 (FERM BP-10389) was cultured, and thus, the bacterial cells in 1000 mL of the culture was collected by centrifugation to obtain the resting bacterial cells and then form a suspension thereof. The suspension was charged to a reaction vessel (2000 mL volume) capable of shaking, aerating, controlling temperature, and controlling pH, and a reaction was carried out at 20° C., and pH 7-8, while shaking and aerating. After the reaction for 108 hours, 2-hydroxy-4-pyridinaldoxime was obtained at yield rate of 87% in the reaction. The analysis values of the resulting 2-hydroxy-4-pyridinaldoxime by IR analysis, proton NMR analysis and MS analysis were the same as the values described in Example 3, and thus, the structure of the resulting 2-hydroxy-4-pyridinaldoxime was identified.

Workup

  1. customwas obtained
  2. temperatureThereafter, the reaction solution was cooled to 30° C.
  3. customthus, the bacterial cells in 1000 mL of the culture was collected by centrifugation
  4. customto obtain the resting bacterial cells
  5. customform a suspension
  6. additionThe suspension was charged to a reaction vessel (2000 mL volume) capable
  7. customwas carried out at 20° C.
  8. stirringpH 7-8, while shaking
  9. customAfter the reaction for 108 hours

Sources & evidence

ORD record
ord-f00482d3c37b4f37b5c8369d7c1d4033
Source dataset
uspto-grants-2010_09
Patent number
US07803585B2

Reaction notes

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