Hydrazine hydrate (1:1) → HCID 23130604, compound

HRID 2080165Notes

Reaction equation

HRID 2080165 reaction equation
[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C.O1CCCC1>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH2:16])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23130721HCID 23130721, compound

Product 1

HCID 23130604HCID 23130604, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(5-Phenoxymethyl-pyridin-2-ylmethyl)-isoindol-1,3-dione described in Preparation Example 188 (383 mg, 1.11 mmol) was dissolved in ethanol (3 mL) and tetrahydrofuran (3 mL). Hydrazine monohydrate (538 μL, 11.1 mmol) was added to this solution at room temperature, and the solution was stirred under reflux for 1 hour. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, washed with brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=10/1), and the title compound (122 mg, 51%) was obtained as a colorless oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe reaction solution was partitioned in water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. customthe solvent was evaporated in vacuo
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-25f6dea0cb1642408ee215ea3c1c0b29
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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