Sodium Cyanide → HCID 67132120, compound

HRID 245024Notes

Reaction equation

HRID 245024 reaction equation
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12].[C:13]1(=O)[CH2:16][CH2:15][CH2:14]1>C(O)(=O)C>[F:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[NH:4][C:13]1([C:1]#[N:2])[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 14496CyclobutanoneHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 67132120HCID 67132120, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.194 g, 4 mmol) was added to a mixture of 4-amino-3-fluorophenol (0.29 g, 2.28 mmol) and cyclobutanone (0.175 g, 2.5 mmol) in 90% acetic acid (3 ml). The reaction mixture was stirred at room temperature for 15 hours. The medium was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 90:10) to yield 1-(2-fluoro-4-hydroxyphenylamino)-cyclobutanecarbonitrile (53b) (0.271 g, 1.31 mmol, 58%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 2.13-2.20 (m, 2H), 2.36-2.41 (m, 2H), 2.70 2.75 (m, 2H), 4.00 (bs, 1H), 6.46 (bs, 1H), 6.52 (ddd, J1=2.2 Hz, J2=0.65 Hz, J3=0.22 Hz, 1H), 6.57 (d, J=2.3 Hz), 6.62 (dd, Jf=3.0 Hz, J2=0.67 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 15.7, 34.1, 50.9, 104.0 (d, J=21.9 Hz), 111.0 (d, J=3.4 Hz), 115.8 (d, J=3.7 Hz), 121.8, 125.3 (d, J=12.3 Hz), 150.1 (d, J=10.4 Hz), 152.8 (d, J=239.3 Hz).

Workup

  1. washThe medium was washed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane:acetone, 90:10)

Sources & evidence

ORD record
ord-8000edcd3577429b941e94697bcfb82a
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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