Dichloromethane → 4-(6-(Fluoromethyl)pyridin-2-yl)but-3-yn-1-amine

HRID 1189244Notes

Reaction equation

HRID 1189244 reaction equation
O.NN.[F:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]#[C:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:9]=[CH:8][CH:7]=1.C(Cl)Cl>CCO>[F:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]#[C:13][CH2:14][CH2:15][NH2:16])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 665979512-(4-(6-(Fluoromethyl)pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dione

Product 1

HCID 665983324-(6-(Fluoromethyl)pyridin-2-yl)but-3-yn-1-amineYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine hydrate (1.0 mL, 5.2 mmol) was added to a solution of 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dione (320 mg, 1.04 mmol) in EtOH (3 mL) and the reaction mixture was stirred for 4 hours at 50° C. The mixture was cooled down, DCM was added and the aqueous phase was extracted. The organic phase was washed with saturated solution of NaHCO3, dried over Na2SO4, filtered and concentrated to yield 117 mg (0.66 mmol, 63%) of 4-(6-(fluoromethyl)pyridin-2-yl)but-3-yn-1-amine as a white solid.

Workup

  1. temperatureThe mixture was cooled down
  2. extractionthe aqueous phase was extracted
  3. washThe organic phase was washed with saturated solution of NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccafe94eeab140cba6a9d8ee8f0449a3
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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