Sodium Hydroxide → 1344145-00-1

HRID 2276746Notes

Reaction equation

HRID 2276746 reaction equation
[F:1][C:2]1[C:3]([C:8]2([NH:12]C(=O)OC)[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[C:3]([C:8]2([NH2:12])[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67451898HCID 67451898, compound

Product 1

HCID 674527091344145-00-1Yield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a 20 mL microwave reaction vial was added methyl 1-(3-fluoropyridin-2-yl)cyclobutylcarbamate (1.47 g, 6.56 mmol, 1.0 equiv), ethanol (12 mL) and 3N aqueous sodium hydroxide (7 mL). The reaction mixture was heated in the microwave reactor at 150° C. for 30 min. The ethanol was evaporated under reduced pressure and the mixture was extracted with ethyl acetate (30 mL). The aqueous layer was then extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to give 1-(3-fluoropyridin-2-yl)cyclobutanamine (1.01 g, 93%) as a crude yellow oil that was used without further purification.

Workup

  1. customTo a 20 mL microwave reaction
  2. customThe ethanol was evaporated under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate (30 mL)
  4. extractionThe aqueous layer was then extracted with ethyl acetate (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-87451847dc3c419db5dbe195ea2f3bde
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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