Sodium Chloride → 3-(2-Amino-2-methylpropyl)aniline

HRID 1858323Notes

Reaction equation

HRID 1858323 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:12]C(=O)C)([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Cl-].[Na+]>C(O)CO>[NH2:12][C:9]([CH3:11])([CH3:10])[CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2×HCID 22125188N-[2-(3-aminophenyl)-1,1-dimethyl-ethyl]-acetamide

Product 1

HCID 221250963-(2-Amino-2-methylpropyl)anilineYield 88%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
195 °C

Procedure

A solution of 1.7 g (8.3 mmol) of N-[2-(3-aminophenyl)-1,1-dimethyl-ethyl]-acetamide in 20 ml of ethylene glycol was treated with 3 g (75 mmol) of sodium hydroxide and the mixture heated at 195° C. for 20 hours. The mixture was cooled and added to 150 ml of 1M aqueous sodium hydroxide saturated with sodium chloride. The product was extracted with diethyl ether (3×100 ml). The combined organic phases were dried over magnesium sulfate, filtered and evaporated to give 1.2 g (88%) of 3-(2-amino-2-methyl-propyl)-aniline as a colorless oil. [Mass spectrum (ESI) M+CH3CN+ =206].

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted with diethyl ether (3×100 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6bf7d007174e46db9ecaaa3b5b33dd91
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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