Ethanol → 4-(2-Amino-2-methylpropyl)aniline

HRID 329909Notes

Reaction equation

HRID 329909 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]([CH3:19])([CH3:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.C(O)C.NN>[Ni]>[NH2:6][C:7]([CH3:19])([CH3:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321Hydrazine2×HCID 138976432-Amino-2-methyl-1-(4-nitrophenyl)propane sulfate

Product 1

HCID 2515564-(2-Amino-2-methylpropyl)aniline

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
40 °C

Procedure

2-Amino-2-methyl-1-(4-nitrophenyl)propane sulfate (6.07 g, 25 mmol) was suspended in ethanol (33 ml, 50 mmol) was added with stirring. Hydrazine (2.5 g, 78 mmol) was added, followed by Raney nickel (0.2 ml of 50% slurry). After 1 min gas evolution began, and the mixture turned yellow and was warmed to about 40° C. After 20 min gas evolution has almost ceased. Fresh catalyst was added and the mixture was boiled with stirring for 5 min to decompose excess hydrazine. After cooling, the suspension was filtered, the catalyst was washed with ethanol, and the filtrates were evaporated. The residue was extracted with diethyl ether (3×40 ml), and the extracts were dried (K2CO3) and evaporated, leaving a yellow oil, which solidified (3.87 g); mp 82-84° C.

Workup

  1. additionwas added
  2. waitAfter 20 min gas evolution has almost ceased
  3. additionFresh catalyst was added
  4. stirringwith stirring for 5 min
  5. temperatureAfter cooling
  6. filtrationthe suspension was filtered
  7. washthe catalyst was washed with ethanol
  8. customthe filtrates were evaporated
  9. extractionThe residue was extracted with diethyl ether (3×40 ml)
  10. dry with materialthe extracts were dried (K2CO3)
  11. customevaporated
  12. customleaving a yellow oil, which

Sources & evidence

ORD record
ord-f4f5a8ecefad40f1b19b5a61a41069c5
Source dataset
uspto-grants-1990_01
Patent number
US04894219

Reaction notes

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