Acrylic Acid → HCID 21254833, compound

HRID 2287595Notes

Reaction equation

HRID 2287595 reaction equation
[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8](Br)=[CH:7][N:6]=1)(=[O:3])[CH3:2].C(N(CCCC)CCCC)CCC.[C:26]([OH:30])(=[O:29])[CH:27]=[CH2:28].C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8](/[CH:28]=[CH:27]/[C:26]([OH:30])=[O:29])=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 6581Acrylic AcidHCID 7622TributylamineHCID 516892Sodium BicarbonateHCID 9019482-Acetylamino-5-bromo-3-methylpyridine

Product 1

HCID 21254833HCID 21254833, compoundYield 84.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-acetamido-5-bromo-3-methylpyridine (110 mg) and tri-n-butylamine (196 mg) in xylene were added palladium(II) acetate (1 mg) and triphenylphosphine (1 mg) under nitrogen atmosphere, and the mixture was heated at 150° C. Acrylic acid (41.5 mg) was added thereto, and the mixture was stirred for 7 hours at the same temperature. After cooling to ambient temperature, ethyl acetate and saturated sodium bicarbonate solution were added to the reaction mixture, and separated aqueous layer was adjusted to pH 4 with 4N hydrochloric acid. The mixture was extracted with chloroform. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was collected by filtration and washed with diisopropyl ether to give (E)-3-(6-acetamido-5-methylpyridin-3-yl)acrylic acid (89 mg).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customseparated aqueous layer
  3. extractionThe mixture was extracted with chloroform
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. filtrationThe residue was collected by filtration
  8. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-53b6377a4f1c4bee93242e57997ce5a2
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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