Sodium Bicarbonate → HCID 13938914, compound

HRID 255569Notes

Reaction equation

HRID 255569 reaction equation
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[C:3](=O)[CH2:4][CH3:5].[O-:13][C:14]#[N:15].[K+].C(=O)(O)[O-].[Na+]>Cl>[CH2:4]([C:3]1[NH:15][C:14](=[O:13])[O:1][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH3:5]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 139389131-Hydroxy-1-(4-pyridinyl)-2-butanone

Product 1

HCID 13938914HCID 13938914, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

1-Hydroxy-1-(4-pyridyl)butan-2-one (26.4 g, 0.16 mol) was dissolved in 350 ml of 2N HCl. Potassium cyanate (38.9 g, 0.48 mol) was added portionwise to this solution over a period of one hour with stirring. After the addition was complete, concentrated hydrochloric acid was added until the pH of the solution was one. After an additional hour the reaction mixture was made basic by addition of sodium bicarbonate solution and the resulting mixture was stirred overnight. The resulting solid precipitated was collected and recrystallized twice from 50% aqueous ethanol to yield the title compound (14.4 g, 47% of theoretical yield), m.p. 287°-289° C. (dec.).

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred overnight
  3. customThe resulting solid precipitated
  4. customwas collected
  5. customrecrystallized twice from 50% aqueous ethanol

Sources & evidence

ORD record
ord-21912e06a8f0409c8d21c32ef928cdc3
Source dataset
uspto-grants-1987_10
Patent number
US04698353

Reaction notes

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