Formaldehyde → N1,6-dimethylbenzene-1,3-diamine

HRID 372624Notes

Reaction equation

HRID 372624 reaction equation
NC1C=C([N+]([O-])=O)C=CC=1C.OS(O)(=O)=O.C=O.[OH-].[Na+].[CH3:21][NH:22][C:23]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:24]=1[CH3:32]>O.[Pd]>[CH3:21][NH:22][C:23]1[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:24]=1[CH3:32]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 74442-Methyl-5-NitroanilineHCID 14798Sodium HydroxideHCID 13317617N,2-dimethyl-5-nitroaniline

Product 1

HCID 14647189N1,6-dimethylbenzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

15.4 g. (0.1M) of 2-amino-4-nitrotoluene was dissolved in 100 ml. 96% H2SO4 at room temperature with stirring and 50 ml. of a 36% solution of formaldehyde in H2O was added. The mixture was stirred for 30 minutes and poured on ice, neutralized with NaOH, filtered and washed. There was obtained 16.1 g. of 2-methylamino-4-nitrotoluene; m.p. 107°-108° (Gnehm/Blume. Ann. 304, 100, gives 107.5° C). 8.3 g. of the above compound was reduced catalytically with Pd as catalyst and the free amine produced was reacted with HCl to form 10 g. of the dihydrochloride (the free amine is liquid). ##STR9##

Workup

  1. additionpoured on ice
  2. filtrationfiltered
  3. washwashed
  4. customThere was obtained 16.1 g
  5. customm.p. 107°-108° (Gnehm/Blume. Ann. 304, 100, gives 107.5° C)

Sources & evidence

ORD record
ord-378daca2bbec4b98ab84c6e6730b020e
Source dataset
uspto-grants-1978_05
Patent number
US04092102

Reaction notes

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