Dimethylformamide → HCID 58707377, compound

HRID 450844Notes

Reaction equation

HRID 450844 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].Br[CH:18](OCC)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].[CH3:30]N(C=O)C>C(OCC)(=O)C>[NH2:11][C:10]1[C:9]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:8]=2[O:7][C:18]=1[C:19](=[O:20])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[O:4][CH2:1][CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 143886552-Hydroxy-3-methylbenzonitrileHCID 86607638HCID 86607638, compound

Product 1

HCID 58707377HCID 58707377, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of potassium carbonate (1.24 g, 8.9 mmol), 2-hydroxy-3-methylbenzonitrile (0.3 g, 2.25 mmol) and ω-bromo-2-ethoxyacetophenone (0.55 g, 2.25 mmol) in dry DMF (10 ml) is stirred at 60° C. for 20 h. The reaction mixture is diluted with ethyl acetate and the resulting solution is washed repeatedly with brine. Drying of the solution over sodium sulfate, filtering and evaporation of the solvent leaves the crude product. Purification on silicagel yields the title compound in pure form. (CDCl3, 400 MHz): 7.53 (d, 2H); 7.41 (m, 2H); 7.14-6.99 (m, 3H); 5.79 (bs, 2H); 4.09 (q, 2H); 2.36 (s, 3H); 1.17 (t, 3H).

Workup

  1. washthe resulting solution is washed repeatedly with brine
  2. dry with materialDrying of the solution over sodium sulfate
  3. filtrationfiltering
  4. customevaporation of the solvent
  5. customleaves the crude product
  6. customPurification on silicagel

Sources & evidence

ORD record
ord-07656deb32304cde8041f5b6830f21f7
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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