Methyl Acrylate → HCID 69653027, compound

HRID 1937024Notes

Reaction equation

HRID 1937024 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH2:20].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][O:17][C:18]([CH:19]=[CH:20][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1)=[O:21]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 15429321HCID 15429321, compound

Product 1

HCID 69653027HCID 69653027, compoundYield 102.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 7-bromo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one (528 mg, 2.0 mmol), acrylic acid-methyl ester (0.36 ml, 4.0 mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.1 mmol) and triethylamine (0.56 ml, 4.0 mmol) in DMF (25 ml) is stirred for 3 hours at 120° C. The batch is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Purification of the residue on silica gel with dichloromethane-ethanol yields 550 mg (99%) of product.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. customPurification of the residue on silica gel with dichloromethane-ethanol

Sources & evidence

ORD record
ord-df4689ddd9e44b1bb2f216808c09277d
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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