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

HRID 550595Notes

Reaction equation

HRID 550595 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-32d89bb6a91c4421868a5048b955acc7
Source dataset
uspto-grants-2011_05
Patent number
US07947686B2

Reaction notes

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