Acetone → HCID 18676096, compound

HRID 1635485Notes

Reaction equation

HRID 1635485 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.[CH3:12][C:13]([CH3:15])=[O:14].C[O-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:12][C:13](=[O:14])[CH3:15])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 18676096HCID 18676096, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-aminobenzoate (7 g, 46.36 mmol) in THF (150 mL) was added acetone (7.5 g, 102 mmol). The solution was warmed to 35° C. where sodium methoxide (3 g, 55.63 mmol) was added sequentially over 20 minutes. The mixture was stirred for 30 minutes, and then brought to reflux for 3 hours. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate. The resulting solution was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1-(3-aminophenyl)-1,3-butanedione as a brown oil (3.1 g, 37%). This oil was used in the next step without further purification.

Workup

  1. additionwas added sequentially over 20 minutes
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. washThe resulting solution was washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93cb915c3c464d27a79aa49fdbefc03d
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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