N-Methylaniline → HCID 20184116, compound

HRID 255693Notes

Reaction equation

HRID 255693 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1>Cl>[ClH:9].[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 20184116HCID 20184116, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 59 g (0.55 mole) of N-methylaniline, stirred and heated at 115°-120° C. under nitrogen atmosphere was added 79 g (0.50 mole) of 2-chloro-3-nitropyridine in four portions at 15 minute intervals. The melt was maintained at 120°-125° C. for 1 hr and then poured into 700 ml of dilute aqueous hydrochloric acid. The precipitate was collected by filtration and dried. The solid was dried and recrystallized as the hydrochloride salt from ethyl acetate-ethereal hydrogen chloride to give 88.3 g (66%) yellow solid. A portion was recrystallized from ethyl acetate-ethyl alcohol to give yellow solid, m.p. 181°-182° C. after undergoing phase changes from 165°-170° C. and at 179° C.

Workup

  1. temperatureheated at 115°-120° C. under nitrogen atmosphere
  2. temperatureThe melt was maintained at 120°-125° C. for 1 hr
  3. filtrationThe precipitate was collected by filtration
  4. customdried
  5. customThe solid was dried
  6. customrecrystallized as the hydrochloride salt from ethyl acetate-ethereal hydrogen chloride

Sources & evidence

ORD record
ord-9aa01103d2a94ab989e25af64693ee3d
Source dataset
uspto-grants-1987_10
Patent number
US04698430

Reaction notes

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