Sodium Hydroxide → (2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine

HRID 715366Notes

Reaction equation

HRID 715366 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.[OH-].[Na+]>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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 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 monohydrate (0.13 mL, 2.74 mmol) 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, Step-3) in methanol (20 mL) and stirred at 50° C. for 20 hours. The reaction mixture is poured into 2 M aqueous sodium hydroxide solution (10 mL) and extracted with DCM (30 mL×3). The organic layer is dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo to give 0.41 g (95% yield) of the title compound as white solid. This material is used for the next reaction without further purification.

Workup

  1. extractionextracted with DCM (30 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-914ff766581148208ca79436d9ce475b
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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