Potassium Carbonate → HCID 178479536, compound

HRID 606925Notes

Reaction equation

HRID 606925 reaction equation
[ClH:1].[NH2:2][OH:3].[C:4]1([C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:19]=2)[C:17]#[N:18])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[OH:3][NH:2][C:17](=[NH:18])[C:16]1[CH:19]=[C:12]([C:11]#[C:10][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 28223905-(2-phenylethynyl)nicotinonitrile

Product 1

HCID 178479536HCID 178479536, compound

Procedure

Add hydroxylamine hydrochloride (0.55 g, 7.8 mmol) to a suspension of 5-phenylethynylnicotinonitrile (0.20 g, 0.98 mmol) and potassium carbonate (0.68 g, 4.9 mmol) and heat at reflux for 2 h. Cool the reaction mixture to room temperature, filter away any solids and concentrate. Purify by silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes, to obtain the free base of the title compound as a white solid. Dissolve the free base in diethyl ether, add a 1 M solution of hydrogen chloride in diethyl ether (1.1 eq) and collect the resulting precipitated solids by filtration to give the title compound (0.1 g, 37%).

Workup

  1. temperatureheat
  2. temperatureat reflux for 2 h
  3. filtrationfilter away any solids
  4. concentrationconcentrate
  5. customPurify by silica gel chromatography
  6. washeluting with 40:60 ethyl acetate

Sources & evidence

ORD record
ord-8e8b99c73b8f4acab72ed0a28467d69a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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