Hydrazine hydrate (1:1) → 1-[5-(Benzyloxy)pyridin-2-YL]methanamine

HRID 2080161Notes

Reaction equation

HRID 2080161 reaction equation
[CH2:1]([O: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>[CH2:1]([O: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 23130583HCID 23130583, compound

Product 1

HCID 231307231-[5-(Benzyloxy)pyridin-2-YL]methanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(5-Benzyloxy-pyridin-2-ylmethyl)-isoindol-1,3-dione described in Preparation Example 184 (4.10 g, 11.9 mmol) was dissolved in ethanol (40 mL) and tetrahydrofuran (40 mL). Hydrazine monohydrate (5.77 mL, 119 mmol) was added to this solution at room temperature, and the solution was stirred under reflux for 50 minutes. The reaction solution was partitioned in water and ethyl acetate. This organic layer was separated, washed with brine and 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), and the title compound (2.8 g, quantitatively) was obtained as a pale yellow solid.

Workup

  1. temperatureunder reflux for 50 minutes
  2. customThe reaction solution was partitioned in water
  3. customThis 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)

Sources & evidence

ORD record
ord-59b4257a36b04ef291764d2414411739
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…