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

HRID 2048976Notes

Reaction equation

HRID 2048976 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. (0.1 M) 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). ##STR10##

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-67b57b1d67284abc948cc7cbef043a6b
Source dataset
uspto-grants-1980_04
Patent number
US04196145

Reaction notes

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