Acetic Acid → HCID 86725504, compound

HRID 878527Notes

Reaction equation

HRID 878527 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH3:12])=[CH:4][CH:3]=1.[NH:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][N:24]=1)[C:20]#[N:21])[NH2:16].CC(O)=O>CCO>[CH2:11]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:15]([C:17]2[CH:18]=[C:19]([C:20]#[N:21])[CH:22]=[CH:23][N:24]=2)[N:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 201187142-Hydrazinylpyridine-4-carbonitrileHCID 28896399HCID 28896399, compound

Product 1

HCID 86725504HCID 86725504, compoundYield 176.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-methylphenyl)pentane-1,3-dione (370 mg, 1.9 mmol) and 2-hydrazinylisonicotinonitrile (150 mg, 1.1 mmol, PREPARATION 2) in 10 mL EtOH was added 2 mL AcOH. The reaction mixture was heated under reflux conditions overnight before being cooled and concentrated to dryness. The residue was adjusted to pH>8 with saturated aq. K2CO3, then extracted by EtOAc (10 mL×3). The combined organic layers were washed with 20 mL brine, dried over Na2SO4, concentrated, and purified by flash column chromatography (PE/EtOAc=10/1) to give the title compound (560 mg, 77%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.33 (3H, m), 2.38 (3H, s), 2.76 (2H, m), 6.33 (1H, s), 7.15 (4H, m), 7.31 (1H, m), 7.82 (1H, s), 8.42 (1H, m). [M+H] Calc'd for C18H16N4, 289; Found, 289.

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions overnight
  2. temperaturebefore being cooled
  3. concentrationconcentrated to dryness
  4. extractionextracted by EtOAc (10 mL×3)
  5. washThe combined organic layers were washed with 20 mL brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (PE/EtOAc=10/1)

Sources & evidence

ORD record
ord-92f90d768bc94226b74ef0aa50994203
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

Loading…