Sodium Hydroxide → HCID 20271449, compound

HRID 326081Notes

Reaction equation

HRID 326081 reaction equation
N[C:2]1[C:3]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.N([O-])=[O:15].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[OH:15][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20271446HCID 20271446, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20271449HCID 20271449, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-amino-2-(3-cyanopropyl)-5-methylpyridine [from Example 1(c)] (1 g) in diluted sulphuric acid (0.78 ml conc. and 6.5 ml water) was reacted with sodium nitrite (0.59 g in 3 ml water) between 6°-10° C. The pH was brought to 6.5 with sodium hydroxide and the product was extracted with chloroform, chromatographed on silica in chloroform-methanol giving 3-hydroxy-2-(3-cyanopropyl)-5-methylpyridine (0.51 g) m.p. 132.5° C.

Workup

  1. extractionthe product was extracted with chloroform
  2. customchromatographed on silica in chloroform-methanol

Sources & evidence

ORD record
ord-ba41e074b1d04978af88f4ae2592bdb8
Source dataset
uspto-grants-1984_04
Patent number
US04444772

Reaction notes

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