Hydrazine → Methyl 2-(4-aminophenyl)-2-methylpropanoate

HRID 546634Notes

Reaction equation

HRID 546634 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].NN>C(O)C.[Pd]>[CH3:6][O:5][C:3](=[O:4])[C:2]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)([CH3:7])[CH3:1]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 11299024HCID 11299024, compound

Product 1

HCID 584407Methyl 2-(4-aminophenyl)-2-methylpropanoateYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4.68 g of methyl 2-methyl-2-(4-nitrophenyl)-propanoate in 200 mL of ethanol, under argon, is added 0.5 g of palladium-on-charcoal (10%). The suspension is heated at 55° C. and 28 mL of hydrazine are added dropwise at this same temperature, and heating is continued for 3 hours at 55° C. After cooling, the reaction medium is filtered through Celite and the filtrate is concentrated under reduced pressure to give 4 g of 2-(4-aminophenyl)-2-methylpropionic acid methyl ester in the form of a colourless oil, the characteristics of which are as follows:

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. filtrationthe reaction medium is filtered through Celite
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c08f1da126348d28232dbdd85add348
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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