Acetic Acid → HCID 66767158, compound

HRID 1662014Notes

Reaction equation

HRID 1662014 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][CH3:10])=[CH:4][CH:3]=1.[C:11]([CH:14]([C:20]([O:22]CC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=O)[CH3:12].C(O)(=O)C.CO>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:22])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([CH3:12])[N:9]2[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 1363651,3-Diethyl 2-acetylpropanedioateHCID 22636246HCID 22636246, compound

Product 1

HCID 66767158HCID 66767158, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 1-(4-fluorophenyl)-2-methylhydrazine (0.6 g, 4.28 mmol), diethyl 2-acetylmalonate (0.96 g, 4.75 mmol), and acetic acid (0.51 g, 8.49 mmol) in water (15 mL) is heated at 115° C. for 3 hours. The reaction is cooled and extracted with EtOAc twice. The organic phase is washed with saturated aqueous sodium chloride, dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel, eluting with DCM:MeOH (from 150:1 to 60:1) to afford the title compound (0.59 g, 49.5% yield). MS (m/z): 279 (M+H).

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with EtOAc twice
  3. washThe organic phase is washed with saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica gel
  7. washeluting with DCM

Sources & evidence

ORD record
ord-c85d00b754bb40f3b921767c95e61478
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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