3-Amino-1,2-propanediol → 3-[(3-Nitropyridin-4-yl)amino]propane-1,2-diol

HRID 329765Notes

Reaction equation

HRID 329765 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15]>C(O)(C)C>[OH:16][CH:13]([CH2:14][OH:15])[CH2:12][NH:11][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 147739133-[(3-Nitropyridin-4-yl)amino]propane-1,2-diolYield 33.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-3-nitropyridine (1.1 g, 6.94 mmol) and 3-amino-1,2-propanediol (1.22 g, 13.4 mmol) in isopropanol (50 ml) was stirred at 20°-25° C. for 20 hours and then concentrated under reduced pressure. Flash chromatography of the residue over silica gel and elution with 10% MeOH-90% CHCl3 gave pure 4-(2,3-dihydroxy-1-propylamino)-3-nitropyridine (500 mg, 33.8%). An analytically pure sample, m.p. 131°-35° C., was obtained upon recrystallization from MeOH-EtOAc-hexane.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washFlash chromatography of the residue over silica gel and elution with 10% MeOH-90% CHCl3

Sources & evidence

ORD record
ord-823f5a69dfb74d6d833a9a7c0be4463e
Source dataset
uspto-grants-1990_01
Patent number
US04892951

Reaction notes

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