Hydrazine → Methyl 3-amino-2,2-dimethylpropanoate

HRID 1921082Notes

Reaction equation

HRID 1921082 reaction equation
NN.O=C1C2C(=CC=CC=2)C(=O)[N:5]1[CH2:14][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17]>CO.C(OCC)C>[NH2:5][CH2:14][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 11173032methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 13285789Methyl 3-amino-2,2-dimethylpropanoateYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

Hydrazine (1.1 eq., 0.27 mL, 8.42 mmol) was added to the solution of methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,2-dimethylpropanoate (0.2 g, 7.66 mmol) in methanol (60 mL) maintained under magnetic stirring at 65° C. After 5 hours the reaction mixture was allowed to cool to room temperature, diluted with diethyl ether and filtered. The filtrate was washed thoroughly with diethyl ether. The title compound was obtained after evaporation of the solvents and it was used in the next step without any further purification. (0.8 g, 75% yield).

Workup

  1. temperaturemaintained
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe filtrate was washed thoroughly with diethyl ether

Sources & evidence

ORD record
ord-9114e9f0bb9e4cc5bda8ad14c0a5cb05
Source dataset
uspto-grants-2012_05
Patent number
US08173659B2

Reaction notes

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