Isopropanol → 6-Methoxy-3-nitro-N-propylpyridin-2-amine

HRID 1285524Notes

Reaction equation

HRID 1285524 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.C(O)(C)C.[CH2:17]([NH2:20])[CH2:18][CH3:19]>O>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH:20][CH2:17][CH2:18][CH3:19])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 7852PropylamineHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 30239126-Methoxy-3-nitro-N-propylpyridin-2-amineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a stirred and cooled (water bath) mixture of 188.6 g (1 mole) of 2-chloro-6-methoxy-3-nitropyridine and 200 ml of isopropanol, 141.9 g (2.4 mole) of n-propylamine are added drop by drop in the course of about 3 hours at a maximum temperature of 25° C. Stirring is continued overnight and then 1000 ml of water are added; the precipitated product is filtered off by suction, washed with water and then dried. The product obtained thereby is intensively yellow colored with a melting point of 69°-70° C. in a yield of 98% of theory.

Workup

  1. temperaturecooled
  2. additionare added drop by drop in the course of about 3 hours at a maximum temperature of 25° C
  3. stirringStirring
  4. filtrationthe precipitated product is filtered off by suction
  5. washwashed with water
  6. customdried
  7. customThe product obtained

Sources & evidence

ORD record
ord-80b2236dd8534ad991d6b05df73fd021
Source dataset
uspto-grants-1986_01
Patent number
US04567272

Reaction notes

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