Water → HCID 22125118, compound

HRID 1858326Notes

Reaction equation

HRID 1858326 reaction equation
[CH2:1]([C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)([CH2:6][CH3:7])[C:4]#[N:5])[CH3:2].O.O.NN>C(O)C>[NH2:14][C:10]1[CH:9]=[C:8]([C:3]([CH2:6][CH3:7])([CH2:1][CH3:2])[C:4]#[N:5])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 22125074HCID 22125074, compound

Product 1

HCID 22125118HCID 22125118, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3.2 g (14.7 mmol) of 2-ethyl-2-(3-nitro-phenyl)-butyronitrile in 50 ml of ethanol was treated with 350 mg of water-wet Raney nickel and the mixture heated to 60° C. 10 ml of hydrazine hydrate was added dropwise over 20 minutes and the reaction stirred for a further 1 hour at 60° C. The cooled mixture was filtered through hyflo filter aid and evaporated to give 2.5 g (90%) of 2-(3-amino-phenyl)-2-ethyl-butyronitrile as an orange oil. [Mass spectrum (ESI) MH+ =189].

Workup

  1. filtrationThe cooled mixture was filtered through hyflo
  2. filtrationfilter aid
  3. customevaporated

Sources & evidence

ORD record
ord-f8d29a24f49b4a7c9e6a8679afeae2ea
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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