m-Toluidine → 1-(3-Methylanilino)phthalazine

HRID 2054181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054181
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1>C(O)CCC>[CH3:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[NH:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1

Komponenten

4

Edukt 2

HCID 7934m-ToluidineHCID 223864641-Chlorophthalazine hydrochloride

Produkt 1

HCID 223864691-(3-Methylanilino)phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Under a N2 atmosphere, 30 g (149 mmol) 1-chlorophthalazine hydrochloride in 0.6 l n-butanol is mixed with 16.2 ml (149 mmol) m-toluidine and stirred for 1 h at 65° C. The solution is concentrated by evaporation and the residue distributed between dichloromethane/MeOH 10:1 and Na2CO3 solution (80 g in 0.5 l H2O). The aqueous phase is extracted twice with dichloromethane/MeOH 10:1, the organic phases are washed with Na2CO3 solution (80 g in 0.5 l H2O) and brine, dried (Na2SO4) and evaporated. The residue is taken up in 200 ml boiling dichloromethane/acetone 1:1, filtered hot, and partly evaporated. Then addition of DIPE leads to crystallization of the title compound, which is filtered off and washed with DIPE: m.p. 176-177° C.; 1H-NMR (DMSO-d6) 9.12 (s, HN), 9.08 (s, 1H), 8.59 (m, 1H), 7.99 (m, 3H), 7.76 (s, 1H), 7.73 (d, 1H), 7.24 (t, 1H), 6.86 (d, 1H), 2.32 (s, 3H); FAB-MS (M+H)+=236; an. calc. (C15H13N3.0.05 H2O) C, 76.28%; H, 5.59%; N, 17.79%; meas. C, 76.04%; H, 5.53%; N, 17.68%.

Aufarbeitung

  1. concentrationThe solution is concentrated by evaporation
  2. extractionThe aqueous phase is extracted twice with dichloromethane/MeOH 10:1
  3. washthe organic phases are washed with Na2CO3 solution (80 g in 0.5 l H2O) and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. filtrationfiltered hot
  7. custompartly evaporated
  8. additionThen addition of DIPE
  9. customleads to crystallization of the title compound, which
  10. filtrationis filtered off
  11. washwashed with DIPE

Quellen und Nachweise

ORD-Eintrag
ord-6b8878097b5a4253ba440dbf1a90ed82
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329660B2

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