Hydrazine hydrate (1:1) → (2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine

HRID 623463Notes

Reaction equation

HRID 623463 reaction equation
O.NN.[CH3:4][O:5][C:6]1[C:11]([CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:10][CH:9]=[C:8]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:7]=1>CO>[CH3:4][O:5][C:6]1[C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=[C:8]([O:24][CH2:25][C:26]([F:29])([F:27])[F:28])[N:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 675086782-((2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 67509640(2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine hydrate (0.13 mL) is added to a solution of 2-((2-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione (0.67 g, 1.83 mmol) in methanol (20 mL) and stirred for 20 hours at 50° C. After removal of the solvent, the residue is poured into 2N sodium hydroxide (10 mL) and extracted with dichloromethane (30 mL×3) and dried over sodium sulfate, and concentrated in vacuo to give 0.41 g (95% yield) of the title compound as a white solid.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue is poured into 2N sodium hydroxide (10 mL)
  3. extractionextracted with dichloromethane (30 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-235c0d75ea474c72927c5f3b023e2214
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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