Isopropanol → 2-(6-Methoxy-3-nitro-2-pyridylamino)ethanol

HRID 1285525Notes

Reaction equation

HRID 1285525 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH:13]([OH:16])(C)[CH3:14].[NH2:17]C(O)C.[OH-].[Na+]>O>[OH:16][CH2:13][CH2:14][NH:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 522583Acetaldehyde ammoniaHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 30239152-(6-Methoxy-3-nitro-2-pyridylamino)ethanolYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 188.6 g (1 mole) of 2-chloro-6-methoxy-3-nitropyridine with 350 ml of isopropanol, 83.5 g (1.4 mole) of aminoethanol are added drop by drop with cooling while stirring and maintaining a temperature of 25°-30° C. After the addition, the reaction mixture is continued to be stirred for another hour at a maximum of 30° and then 47.5 ml of 50% caustic soda solution are added drop by drop over the course of about 2 hours at a maximum temperature of 30° C. After 6 hours of stirring, 500 ml of water are stirred in and the product is filtered off with suction, is then washed sufficiently with water and is then dried. The compound is obtained in the form of a yellow powder with a melting point of 121°-2° C. and in a yield of 95.5% of theory.

Workup

  1. additionare added drop by drop
  2. temperaturewith cooling
  3. temperaturemaintaining a temperature of 25°-30° C
  4. additionAfter the addition
  5. stirringto be stirred for another hour at a maximum of 30°
  6. stirringAfter 6 hours of stirring
  7. filtrationis filtered off with suction
  8. washis then washed sufficiently with water
  9. customis then dried
  10. customThe compound is obtained in the form of a yellow powder with a melting point of 121°-2° C. and in a yield of 95.5% of theory

Sources & evidence

ORD record
ord-912784713a0642bab43b77e0ab8b3068
Source dataset
uspto-grants-1986_01
Patent number
US04567272

Reaction notes

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