4-Chloroaniline → 1-(4-Chloroanilino)phthalazine

HRID 49911

Reaktionsgleichung

Reaktionsgleichung von HRID 49911
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.C1C=C2C=NNC(=O)C2=CC=1.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>C(O)CCC>[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[N:4][N:3]=2)=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 78124-ChloroanilineHCID 83941(2H)-PhthalazinoneHCID 1607931-Chlorophthalazine

Produkt 1

HCID 227419971-(4-Chloroanilino)phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

30 g (149 mmol) 1-chlorophthalazine (prepared from phthalazone in the manner described under Example 67A.1) and 20 g (157 mmol) 4-chloroaniline are heated in 630 ml n-butanol for 30 min to 65° C. The crude product is filtered off, washed with ether, taken up in 2 l di-chloromethane/methanol 9:1, and washed with sat. NaHCO3 solution and brine. The aqueous phases are extracted three times with dichloromethane/methanol 9:1, the organic phases dried (Na2SO4), and evaporated to a residual volume of ≈50 ml, leading to crystallization of the title compound: m.p.: 211° C.; Anal. calc.(C14H10N3Cl) C, 65.76%; H, 3.94%; N, 16.43%, Cl, 13.86%. found C, 66.02%; H, 3.92%; N, 16.53%, Cl, 13.51%.

Aufarbeitung

  1. filtrationThe crude product is filtered off
  2. washwashed with ether
  3. washwashed with sat. NaHCO3 solution and brine
  4. extractionThe aqueous phases are extracted three times with dichloromethane/methanol 9:1
  5. dry with materialthe organic phases dried (Na2SO4)
  6. customevaporated to a residual volume of ≈50 ml
  7. customleading to crystallization of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-533cdc17081f491db89c781699e36145
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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