Water → C-(5-(2-Cyclopropylvinyl)thiophen-2-yl)methylamine

HRID 2080141Notes

Reaction equation

HRID 2080141 reaction equation
[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][N:12]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.O.NN.[OH-].[Na+].O>C(O)C>[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][NH2:12])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 671195832-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione

Product 1

HCID 67119557C-(5-(2-Cyclopropylvinyl)thiophen-2-yl)methylamineYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione described in Preparation Example 150 (330 mg, 1.02 mmol) was dissolved in ethanol (50 mL), hydrazine monohydrate (500 mg, 10 mmol) was added thereto, and the solution was stirred under reflux for 2 hours. After cooling to room temperature, 2N sodium hydroxide solution (10 mL) and water (100 mL) were added to the reaction solution, which was then washed twice with hexane (50 mL). The organic layer was dried over anhydrous sodium sulfate, then, the solvent was evaporated in vacuo, and the title compound (180 mg, 1.01 mmol, 98.6%) was obtained as a colorless oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. washwas then washed twice with hexane (50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-527b9a0adfba491888f8de2e74143a9a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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