Methanol → HCID 23130641, compound

HRID 2080102Notes

Reaction equation

HRID 2080102 reaction equation
[N:1]1[N:2]([CH2:6][CH2:7][CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[N:3]=[CH:4][CH:5]=1.O.NN.CO>CO.O1CCCC1>[N:1]1[N:2]([CH2:6][CH2:7][CH2:8][NH2:9])[N:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 23130809HCID 23130809, compound

Product 1

HCID 23130641HCID 23130641, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture solution of 2-(3-[1,2,3]triazol-2-yl-propyl)-isoindol-1,3-dione (1782 mg, 6.95 mmol) in methanol-tetrahydrofuran (5:4, 27 mL) was added hydrazine monohydrate (371 μl, 7.65 mmol), and the solution was stirred for 5 days at room temperature. Methanol (8 mL) was added thereto, followed by further stirring for 3.25 hours under reflux. The reaction mixture was filtered, and the filtrate was concentrated. The resulting residue was dissolved in tetrahydrofuran, adsorbed onto NH silica gel, purified by NH silica gel chromatography (ethyl acetate-methanol), and the title compound (491 mg, 1.36 mmol, 19.6%) was obtained.

Workup

  1. stirringby further stirring for 3.25 hours
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in tetrahydrofuran
  6. custompurified by NH silica gel chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-088f64388c4e4cf5abb237a2c3bfe162
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…