Hydrochloric Acid → (E)-3-(6-Acetamidopyridin-3-YL)acrylic acid

HRID 850201Notes

Reaction equation

HRID 850201 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][N:6]=1)(=[O:3])[CH3:2].C(N(CCCC)CCCC)CCC.[C:25]([OH:29])(=[O:28])[CH:26]=[CH2:27].Cl>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.O>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8](/[CH:27]=[CH:26]/[C:25]([OH:29])=[O:28])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 7622TributylamineHCID 2930972-Acetamido-5-bromopyridine

Product 1

HCID 10703461(E)-3-(6-Acetamidopyridin-3-YL)acrylic acidYield 75.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

To a mixture of 2-acetamido-5-bromopyridine (240 mg), tri-n-butylamine (456 mg), palladium(II) acetate (0.13 mg) and triphenylphosphine (1.5 mg) in xylene (0.48 ml) was dropwise added acrylic acid (97 mg) at 150° C., and the mixture was stirred for 7 hours at the same temperature. After cooling the mixture, water was added thereto, and the mixture was adjusted to pH4 with hydrochloric acid. The precipitate was collected by filtration, washed with xylene and water, and dried to give (E)-3-(6-acetamidopyridin-3-yl)acrylic acid (173 mg) as yellow crystals.

Workup

  1. customat 150° C.
  2. additionwas added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with xylene and water
  5. customdried

Sources & evidence

ORD record
ord-754a4a82512f46fe8d8b16920d0df88e
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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