4-Chloro-N-methylbenzenamine → N-(4-Chlorophenyl)-N-methyl-3-nitropyridin-2-amine

HRID 637825Notes

Reaction equation

HRID 637825 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702724-Chloro-N-methylbenzenamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 13560173N-(4-Chlorophenyl)-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 90 g (0.63 mole) of 4-chloro-N-methylaniline heated to 115°-120° C. under nitrogen atmosphere with stirring was added 66.3 g (0.42 mole) of 2-chloro-3-nitropyridine in four portions over a period of 80 minutes. After stirring the reaction mixture for an additional 20 minutes at 115°-120° C., the temperature was increased to 135°-140° C. for an additional 20 minute period. The hot melt was poured into 700 ml of 2N hydrochloric acid solution. Red precipitate weighing 96 g was collected and dissolved in hot acetic acid and converted to the hydrochloride salt by adding ethereal hydrogen chloride. The yield of the yellow solid was 90 g (72%). A portion of the salt was recrystallized from ethyl acetate-ethyl alcohol. On drying at 80° C. in vacuo, the hydrochloride salt dissociated to the free base, the title compound, m.p. 107°-110° C.

Workup

  1. stirringAfter stirring the reaction mixture for an additional 20 minutes at 115°-120° C.
  2. temperaturethe temperature was increased to 135°-140° C. for an additional 20 minute period
  3. customwas collected
  4. dissolutiondissolved in hot acetic acid
  5. additionby adding ethereal hydrogen chloride
  6. customA portion of the salt was recrystallized from ethyl acetate-ethyl alcohol
  7. customOn drying at 80° C. in vacuo

Sources & evidence

ORD record
ord-a0d1da09e18f41888cc28013e8bbc39d
Source dataset
uspto-grants-1985_12
Patent number
US04558132

Reaction notes

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