Ammonia → 3,4-Dimethylaniline

HRID 1414434Notes

Reaction equation

HRID 1414434 reaction equation
[C:1]1([CH3:12])[C:2]([CH3:11])=[CH:3][C:4](S([O-])(=O)=O)=[CH:5][CH:6]=1.[Na+].[NH2-:14].[Na+].N>>[NH2:14][C:4]1[CH:5]=[CH:6][C:1]([CH3:12])=[C:2]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 23668192Sodium Xylenesulfonate

Product 1

HCID 72483,4-DimethylanilineYield 88.1%

Procedure

In a 200-ml autoclave were placed 35 grams (0.163 moles) of anhydrous sodium 4-o-xylene sulfonate, 14 grams (0.35 mole) of sodium amide and 120 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 120° to 125° C for 15 hours. The reaction pressure in the autoclave was 90 to 100 atm. during the reaction. After the ammonia was removed, 15 ml of methanol was added to the reaction mixture for solvolysis. Thereafter 500 ml of water was added to the product and the mixture was treated in the same manner as in Example 1, whereby 17.4 grams of 3,4-xylidine boiling at 112° C/22 mm Hg was obtained. Yield was 88.1%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition15 ml of methanol was added to the reaction mixture for solvolysis
  5. additionThereafter 500 ml of water was added to the product
  6. additionthe mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-f8f117ef79994f029d7bd52f4f3a31d8
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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