Ammonia → 2-(4-Aminophenyl)ethylamine

HRID 1414441Notes

Reaction equation

HRID 1414441 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](S([O-])(=O)=O)=[CH:6][CH:5]=1.[K+].[NH2-:15].[K+].N>>[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:15])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 87015Potassium amideHCID 23690036Potassium p-(2-aminoethyl)benzene sulfonate

Product 1

HCID 728952-(4-Aminophenyl)ethylamineYield 82.5%

Procedure

In a 200-ml autoclave were placed 12 grams (0.05 mole) of anhydrous potassium p-(2-aminoethyl)benzene sulfonate, 6.1 grams (0.11 mole) of potassium amide and 55 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 135° C for 5 hours. The reaction pressure in the autoclave was 115 atm. during the reaction. After the ammonia was removed, 10 ml of water was added to the reaction mixture for hydrolysis. The product was extracted with ether and the ether was distilled off to produce crude 4-(2-aminoethyl)aniline. The recrystallization thereof from ether gave 5.6 grams of 4-(2-aminoethyl)aniline having a melting point of 62° to 63° C and boiling point of 140° to 142° C/12 mm Hg. Yield was 82.5%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition10 ml of water was added to the reaction mixture for hydrolysis
  5. extractionThe product was extracted with ether
  6. distillationthe ether was distilled off
  7. customto produce crude 4-(2-aminoethyl)aniline
  8. customThe recrystallization

Sources & evidence

ORD record
ord-72ce475e7ab74c4b8748713813b0bed0
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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