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1,4-Dioxane → 2-(3-Chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid

HRID 1413799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1413799
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Br:11])[CH2:5][NH:6][NH2:7].[C:12](=[O:15])([O-])[OH:13].[Na+].[O:17]1[CH2:22][CH2:21]OCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Br:11])[CH2:5][N:6]1[N:7]=[C:9]([CH2:8][C:12]([OH:13])=[O:15])[C:10]2[C:21](=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:22]1=[O:17]
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Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 20495799[(4-Bromo-3-chlorophenyl)methyl]hydrazine

Produkt 1

HCID 204958292-(3-Chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

3-Chloro-4-bromobenzylhydrazine (2.5 g.) was added to a stirred mixture of 3-oxo-Δ1,α-phthalanacetic acid (also known as phthalideneacetic acid) (1.92 g.) and sodium hydrogen carbonate (2.0 g.) in dioxan (50 ml.) and water (25 ml.). The mixture was then heated under reflux for 3 hours, cooled to room temperature and poured into water (200 ml.). The aqueous solution was extracted with ether (3×100 ml.) and the aqueous phase was acidified with concentrated hydrochloric acid to pH 2. The solid which deposited was collected, washed well with water, dried in vacuo, and then recrystallised twice from a mixture of toluene isopropanol and petrol (60-80) (6:2:3 v/v/v) to give 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (0.23 g.), m.p. 184°-186° C.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 3 hours
  3. extractionThe aqueous solution was extracted with ether (3×100 ml.)
  4. customThe solid which deposited was collected
  5. washwashed well with water
  6. customdried in vacuo
  7. customrecrystallised twice from a mixture of toluene isopropanol and petrol (60-80) (6:2:3 v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-c263b125d14a4394ac270b1b12239bcf
Quelldatensatz
uspto-grants-1981_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04251528

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