Sodium Acetate → HCID 67359365, compound

HRID 1664496Notes

Reaction equation

HRID 1664496 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)=[O:4].Cl.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1)#[N:20].CC([O-])=O.[Na+]>CC(O)=O.OS(O)(=O)=O>[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([CH:5]1[CH2:10][C:9]2[C:25]3[C:24](=[CH:23][CH:22]=[C:21]([C:19]#[N:20])[CH:26]=3)[NH:27][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 67359938HCID 67359938, compound

Product 1

HCID 67359365HCID 67359365, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred solution of 4-oxo-cyclohexanecarboxylic acid methyl-phenyl-amide (50 mg, 0.22 mmol) and (4-cyanophenyl)-hydrazine hydrochloric acid salt (36.5 mg, 0.22 mmol) in glacial AcOH (1 ml) is heated to reflux for 1 h. At rt, two drops of conc. H2SO4 are added and the reaction mixture is again heated to reflux for another 1 h, then cooled to rt and poured into 5% aqueous NaOAc. The resulting precipitate is filtered, rinsed several times with H2O and dried under high vacuum providing pure subtitle compound (35 mg) in 49% yield as a white solid. tR (LC-4) 1.06 min; ESI-MS (positive ion): m/z 329.96 [M]+ (calcd 329.40 for C21H19N3O). 1H-NMR (CDCl3): 2.12 (m, 2H); 2.53 (m, 1H); 2.73 (m, 3H); 2.93 (m, 1H); 3.34 (s, 3H); 7.25 (m, 3H); 7.32 (m, 2H); 7.41 (m, 2H), 7.71 (s, 1H); 8.04 (br s, 1H).

Workup

  1. temperatureto reflux for 1 h
  2. temperaturethe reaction mixture is again heated
  3. temperatureto reflux for another 1 h
  4. filtrationThe resulting precipitate is filtered
  5. washrinsed several times with H2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-fb3075212dc54050a7cd01dbdaf6ff80
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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