Acetic Acid → HCID 19734534, compound

HRID 327121Notes

Reaction equation

HRID 327121 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].C(O)(=O)C.[CH:15]([OH:18])([CH3:17])[CH3:16]>>[N:6]1[CH:7]=[CH:8][C:3]([C:1](=[NH:2])[O:18][CH:15]([CH3:17])[CH3:16])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 75064-CyanopyridineHCID 24758Sodium hydride

Product 1

HCID 19734534HCID 19734534, compound

Procedure

4-cyanopyridine (10.0 g, 96.1 mmol) was dissolved in isopropanol (50 ml), and sodium hydride (0.23 g, 9.6 mmol) from which oily matters had been removed by washing with ether was added. The mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was neutralized by adding acetic acid (0.64 g, 10.7 mmol) and concentrated under reduced pressure. To the residual concentrate was added diethyl ether (50 ml). Insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. To this concentrate was added hexane (80 ml), and deposited unreacted 4-cyanopyridine was removed by filtration. The filtrate was concentrated under reduced pressure to give crude isopropyl 4-pyridinecarboximidate (11.0 g) as a pale yellow oil.

Workup

  1. washby washing with ether
  2. additionwas added
  3. concentrationconcentrated under reduced pressure
  4. concentrationTo the residual concentrate
  5. additionwas added diethyl ether (50 ml)
  6. customInsolubles were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo this concentrate was added hexane (80 ml)
  9. customwas removed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f868d4f69ba44ee2a53d0a5f006c8c3b
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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