Water → Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

HRID 1074549

Reaktionsgleichung

Reaktionsgleichung von HRID 1074549
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][NH:3]1.[H-].[Na+].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][C:22]=1[Cl:29].O>CN(C)C=O>[Cl:29][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:21]=1[Br:20])[CH2:25][N:3]1[N:4]=[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 129473921-Bromo-4-(bromomethyl)-2-chlorobenzene

Produkt 1

HCID 20495807Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetateAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate (11.5 g.) and sodium hydride (2.7 g.; 50% w/w dispersion in mineral oil) in dimethylformamide (125 ml.) was stirred at 60° C. for 1 hour under nitrogen. The solution obtained was cooled to room temperature and then 4-bromo-3-chlorobenzyl bromide (15.0 g.) was added, and the mixture stirred at 60° C. for 2 hours. After cooling to 25° C. the reaction mixture was poured into water (500 ml.). The aqueous mixture obtained was extracted with ethyl acetate (400 ml.). The extracts were washed with water, dried (MgSO4), and evaporated to give a solid, which was crystallised from propan-2-ol to yield ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate (7.3 g.), m.p. 142°-145° C.

Aufarbeitung

  1. customThe solution obtained
  2. temperaturewas cooled to room temperature
  3. stirringthe mixture stirred at 60° C. for 2 hours
  4. temperatureAfter cooling to 25° C. the reaction mixture
  5. customThe aqueous mixture obtained
  6. extractionwas extracted with ethyl acetate (400 ml.)
  7. washThe extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a solid, which
  11. customwas crystallised from propan-2-ol

Quellen und Nachweise

ORD-Eintrag
ord-1bee9c7e61074308af24011cd4849793
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04393062

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