4-Nitrotoluene → Benzenamine, N-hydroxy-4-methyl-(9CI)

HRID 1413384Notes

Reaction equation

HRID 1413384 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-])=[O:2].[Cl-].[NH4+]>[Zn].O>[C:7]1([CH3:10])[CH:8]=[CH:9][C:4]([NH:1][OH:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 74734-NitrotolueneHCID 25517Ammonium Chloride

Product 1

HCID 69333Benzenamine, N-hydroxy-4-methyl-(9CI)Yield 19.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

281 g (2.05 moles) of p-nitrotoluene, 125 g (2.35 moles) of ammonium chloride and 4 l of water were charged into a 10-l reaction flask. 310 g (4.74 moles) of zinc dust was added thereto at room temperature (i.e., about 20°-30° C.) over a period of 15 minutes while stirring the mixture, and the mixture was stirred for an additional 30 minutes. In this case, the temperature of the reaction system increased to 65° to 70° C. with stirring. Thereafter, the reaction mixture was filtered, and the filtrate was saturated with sodium chloride. The filtrate was allowed to stand in a cool place for 24 hours. The precipitated crystals were filtered, and recrystallized from 1 l of a benzene-petroleum ether (1:1 by volume) mixture to obtain 50 g of p-tolylhydroxyl amine.

Workup

  1. stirringthe mixture was stirred for an additional 30 minutes
  2. temperatureIn this case, the temperature of the reaction system increased to 65° to 70° C.
  3. stirringwith stirring
  4. filtrationThereafter, the reaction mixture was filtered
  5. waitto stand in a cool place for 24 hours
  6. filtrationThe precipitated crystals were filtered
  7. customrecrystallized from 1 l of a benzene-petroleum ether (1:1 by volume) mixture

Sources & evidence

ORD record
ord-c9d54d92546c429f9ab953e1057a9856
Source dataset
uspto-grants-1981_02
Patent number
US04250117

Reaction notes

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