Hydrochloric Acid → HCID 10444194, compound

HRID 1392253Notes

Reaction equation

HRID 1392253 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[N:8].F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].Cl>C(OCC)(=O)C.CN(C)C=O>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([CH:9]([C:7]#[N:8])[C:10]([O:12][CH3:13])=[O:11])[CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7747Methyl cyanoacetateHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 10444194HCID 10444194, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flask made of glass equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel and having an inner volume of 100 ml were charged 3.03 g (21.9 mmol) of potassium carbonate, 5.0 ml of N,N-dimethylformamide, 2.17 g (21.7 mmol) of methyl cyanoacetate with a purity of 99% and 1.45 g (8.94 mmol) of 2,4-difluoronitrobenzene with a purity of 98% under argon atmosphere, and under stirring, the mixture was reacted at 60° C. for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 50 ml of ethyl acetate was added to the mixture, and 2.9 ml (34.8 mmol) of 12 mol/l hydrochloric acid was gradually added dropwise to the mixture while stirring. Then, the organic layer was separated, and washed successively with 20 ml of water and 30 ml a saturated saline solution in this order, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography (filler: Daisogel 1002W, eluent: toluene) to obtain 1.81 g (isolation yield: 84%) of methyl 2-(5-fluoro-2-nitrophenyl)-2-cyanoacetate as a yellowish oily product with a purity of 99% (areal percentage by high performance liquid chromatography).

Workup

  1. customIn a flask made of glass
  2. customequipped with a stirrer
  3. customthe mixture was reacted at 60° C. for 6 hours
  4. customAfter completion of the reaction
  5. additionwas gradually added dropwise to the mixture
  6. stirringwhile stirring
  7. customThen, the organic layer was separated
  8. washwashed successively with 20 ml of water and 30 ml a saturated saline solution in this order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. concentrationthe resulting concentrate
  13. customwas purified by silica gel column chromatography (filler: Daisogel 1002W, eluent: toluene)

Sources & evidence

ORD record
ord-12b11429472647458336d21c571eac59
Source dataset
uspto-grants-2008_03
Patent number
US07342040B2

Reaction notes

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