Isonicotinic Acid → HCID 21472675, compound

HRID 2295012Notes

Reaction equation

HRID 2295012 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-e2fc89c3f171461296b3b9476b58a3c2
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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