Methyl Acrylate → HCID 22271930, compound

HRID 488667

Reaction equation

HRID 488667 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:40]([O:44]C)(=[O:43])[CH:41]=[CH2:42]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[NH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH2:42][CH2:41][C:40]([OH:44])=[O:43])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 7294Methyl AcrylateHCID 753034-Bromo-1-naphthylamineHCID 80271Tri-o-tolylphosphineHCID 517044Potassium Acetate

Product 1

HCID 22271930HCID 22271930, compoundYield 58.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 16212273Tetrabutylammonium chloride hydrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-1-naphthylamine (4.44 g, 20.0 mmol), potassium acetate (6.28 g, 64.0 mmol), tetrabutylammonium chloride hydrate (6.1 g, 22 mmol), palladium(II)acetate (224 mg, 1.0 mmol) and tri-o-tolylphosphine (1.22 g, 4.0 mmol) was added DMF (60 mL) and methyl acrylate (2.3 mL, 25 mmol). The reaction was heated to 100° C. under N2 for 2 hours, poured into water (300 mL) and extracted with diethyl ether (3×50 mL). The combined ether layers were washed with brine (1×50 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The product was purified on silica gel eluting with 30% ethyl acetate/hexanes to provide the titled compound 2.5 g, 55%).

Workup

  1. extractionextracted with diethyl ether (3×50 mL)
  2. washThe combined ether layers were washed with brine (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified on silica gel eluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-67cb650aaed443c6be9a79aeee2a1e7e
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Linked notes

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