Acetone → HCID 118970840, compound

HRID 930793Notes

Reaction equation

HRID 930793 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].CC(C)=O.C(N(CC)CC)C>C(#N)C>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[CH:20]=[C:15]2[N:14]([CH:2]=1)[CH:19]=[CH:18][CH:17]=[CH:16]2)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 180AcetoneHCID 79752-MethylpyridineHCID 8471TriethylamineHCID 2440252-Bromo-2'-nitroacetophenone

Product 1

HCID 118970840HCID 118970840, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

First, 4.1 mmol of 2-bromo-2′-nitroacetophenone and 5.33 mmol (1.3 eq.) of picoline are dissolved into 12 ml of acetone and the reaction mixture is allowed to react at 90° C. for 3 hours. After the completion of the reaction, the reaction mixture is cooled at room temperature and filtered, and then the filtered solid is washed with 5 ml of dichloromethane. To 20 ml of acetonitrile, 4.1 mmol of the obtained solid and 20.5 mmol (5 eq.) of triethylamine are added. Then, the reaction mixture is allowed to react at 60° C. for 16 hours. After the completion of the reaction, the reaction mixture is concentrated under reduced pressure, and then the concentrated reaction mixture is purified by silica gel column chromatography using hexane:ethyl acetate:dichloromethane=30:1:2 as a solvent to obtain the target compound.

Workup

  1. customto react at 90° C. for 3 hours
  2. customAfter the completion of the reaction
  3. filtrationfiltered
  4. washthe filtered solid is washed with 5 ml of dichloromethane
  5. customto react at 60° C. for 16 hours
  6. customAfter the completion of the reaction
  7. concentrationthe reaction mixture is concentrated under reduced pressure
  8. customthe concentrated reaction mixture
  9. customis purified by silica gel column chromatography
  10. customethyl acetate:dichloromethane=30:1:2 as a solvent to obtain the target compound

Sources & evidence

ORD record
ord-1a1346afa93341bf9cfa083c333b5b24
Source dataset
uspto-grants-2016_03
Patent number
US09296751B1

Reaction notes

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