Ethanol → HCID 11580141, compound

HRID 628826Notes

Reaction equation

HRID 628826 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=C([CH:18]=[CH:19][CH:20]=3)C#N)[CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[OH-:22].[Na+].[CH2:24]([OH:26])[CH3:25]>>[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[C:25]([CH:18]=[CH:19][CH:20]=3)[C:24]([OH:22])=[O:26])[CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 69233193HCID 69233193, compound

Product 1

HCID 11580141HCID 11580141, compound

Procedure

Part B. A solution of 3-(2-p-tolyl-pyrimidin-4-yl)-benzonitrile (87 mg, 0.321 mmol) in ethanol (2 mL) is treated with aq. sodium hydroxide solution (1 mL, 10 N), and the resulting solution is heated to reflux until the starting material is consumed as determined by LC/MS. After being allowed to cool, the solution is evaporated and subjected to aqueous workup. The extract, which contained a mixture of amide and acid compounds, is separated by column chromatography to afford pure title compound (11 mg) as a white solid, m.p. 225-226° C. 1H NMR (300 MHz, DMSO-d6): δ 8.94 (1H, d, J=6 Hz), 8.82 (1H, s), 8.53 (1H, d, J=8 Hz), 8.39 (2H, d, J=9 Hz), 8.11 (1H, d, J=8 Hz), 8.03 (1H, d, J=6 Hz), 7.71 (1H, t, J=8 Hz), 7.37 (2H, d, J=9 Hz), 2.40 (3H, s). MS (ES+): m/e 292 (20), 291 (100). MS (ES−): m/e 290 (20), 289 (100).

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux until the starting material
  3. customis consumed
  4. temperatureto cool
  5. customthe solution is evaporated
  6. additiona mixture of amide and acid compounds
  7. customis separated by column chromatography

Sources & evidence

ORD record
ord-9314e643a9ad4d9489947e3b9cda558c
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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