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

HRID 365586

Reaktionsgleichung

Reaktionsgleichung von HRID 365586
[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]

Komponenten

9

Edukt 4

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

Produkt 1

HCID 10703461(E)-3-(6-Acetamidopyridin-3-YL)acrylic acidAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6c49bb09f0434218a708cc369e424a1f
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127389

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