Glyoxal → HCID 67133190, compound

HRID 545331Notes

Reaction equation

HRID 545331 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([O-])(=O)[CH3:6].[NH4+:9].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.C(C=O)=O>CO>[CH:1]1([N:4]2[CH:6]=[CH:5][N:9]=[C:15]2[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([C:11]([F:21])([F:20])[F:10])[CH:13]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7860GlyoxalHCID 679903-(Trifluoromethyl)benzaldehydeHCID 69828CyclopropylamineHCID 517165Ammonium Acetate

Product 1

HCID 67133190HCID 67133190, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

8.17 ml=6.62 g (113.6 mmol) of cyclopropylamine and 8.90 g (113.6 mmol) of ammonium acetate were added to a solution of 6.80 g (37.9 mmol) of 3-(trifluoromethyl)benzaldehyde in 60 ml of MeOH and the reaction mixture was cooled down to 0° C. While stirring, 9.59 ml=16.49 g (113.6 mmol) of glyoxal solution (40% in water) was added and then the reaction was warmed up to 50° C. After cooling down to RT, the solvents were evaporated and the residue dissolved in water and Et2O. The reaction mixture was extracted three times with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2) to give 1.96 g (21%) of the title compound as light red oil. MS: 253.1 (MH+).

Workup

  1. temperaturethe reaction was warmed up to 50° C
  2. temperatureAfter cooling down to RT
  3. customthe solvents were evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionThe reaction mixture was extracted three times with Et2O
  6. washthe organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-8fc6468d21174d3fabf1415d45c5e170
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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