3-Chloro-2-methylaniline → N-(3-Chloro-2-methylphenyl)-3-nitropyridin-2-amine

HRID 614333Notes

Reaction equation

HRID 614333 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[C:13]([CH3:19])=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[Cl:11][C:12]1[C:13]([CH3:19])=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 12445357N-(3-Chloro-2-methylphenyl)-3-nitropyridin-2-amine

Conditions

Temperature
50 °C

Procedure

A mixture of 6.3 g. (0.04 mole) of 2-chloro-3-nitropyridine and 16.9 g. (0.12 mole) of 3-chloro-2-methylaniline was heated in an oil bath to 170° C. when the temperature spontaneously rose to 185° C. After an additional 10 minutes at 180° C., the mixture was cooled to 50° C. and extracted with a solution of 75 ml. of water and 25 ml. of acetic acid. The insolubles were collected, air dried, dissolved in methylene chloride, and the solution was dried over magnesium sulfate. The solution was concentrated to a small volume and diluted with 50 ml. of ether which caused crystallization of 6.6 g. of 2-(3-chloro-2-methylanilino)-3-nitropyridine, m.p. 134°-135° C.

Workup

  1. additionA mixture of 6.3 g
  2. customspontaneously rose to 185° C
  3. extractionextracted with a solution of 75 ml
  4. customThe insolubles were collected
  5. customair dried
  6. dissolutiondissolved in methylene chloride
  7. dry with materialthe solution was dried over magnesium sulfate
  8. concentrationThe solution was concentrated to a small volume
  9. additiondiluted with 50 ml
  10. customcrystallization of 6.6 g

Sources & evidence

ORD record
ord-e2712bac3eaf4fe58e6e3246ef394e06
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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