Methyl Acrylate → HCID 69652699, compound

HRID 1831750Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][CH2:14][CH2:15][CH:5]3[C:4]=2[CH:3]=1.[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH2:20].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=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:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][CH2:14][CH2:15][CH:5]3[C:4]=2[CH:3]=1)=[O:21]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 4.0 g (15.0 mmol) of 8-bromo-1,2,3,3a,5,9b-hexahydrocyclo-penta[c]quinolin-4-one (DE file number: 198 06 348.2) in 150 ml of DMF is heated for 4 hours to 120° C. with 2.7 ml (30.0 mmol) of acrylic acid-methyl ester, 4.2 ml (30 mmol) of triethylamine, 168 mg (0.75 mmol) of palladium(II) acetate and 457 mg (1.5 mmol) of tri-o-tolyl-phosphine. After 868 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium is added, the batch is stirred for 18 hours at 120° C., diluted at room temperature with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 2.05 g of product.

Workup

washwashed with water
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-72bc5a2db8664ae186cde87ae56e9aa9
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067667B2

Reaction notes

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