Isonicotinic Acid → HCID 21472675, compound

HRID 2396908Notes

Reaction equation

HRID 2396908 reaction equation
[NH2:1][CH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[C:12](O)(=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:9]([O:8][P:4]([CH2:3][CH2:2][NH:1][C:12]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:19])([O:5][CH2:6][CH3:7])=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 5922Isonicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733596Diethyl (2-aminoethyl)phosphonate

Product 1

HCID 21472675HCID 21472675, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diethyl 2-aminoethylphosphonate (12.5 g), isonicotinic acid (10.2 g), 1-hydroxybenzotriazole (11.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.83 g) and dichloromethane (190 ml) was stirred at room temperature for 15 hours. The reaction mixture was washed with aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol-chloroform) to give 7.94 g of N-(2-diethoxyphosphorylethyl)-4-pyridinecarboxamide as an oil.

Workup

  1. washThe reaction mixture was washed with aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (5% methanol-chloroform)

Sources & evidence

ORD record
ord-2c462e42e0ca4f7da4490fde135060f8
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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