O-Xylene → Phthalazine

HRID 1383854

Reaktionsgleichung

Reaktionsgleichung von HRID 1383854
O=[N:2][NH2:3].Cl.C(N(CC)CC)C.[C:12]1([CH3:19])[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1>>[CH:18]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[N:3][N:2]=1

Komponenten

4

Edukt 3

HCID 7237O-XyleneHCID 11130Triethylamine hydrochlorideHCID 37183Nitrosamine

Produkt 1

HCID 9207Phthalazine

Versuchsvorschrift

1,11′-Carbonyldiimidazole-(0.98 g, 6.1 mmol) was added to a stirred mixture of 3-furoic acid (0.68 g, 6.1 mmol) in THF (30 ml). The mixture was stirred for 0.75 h before adding the preceding hydrazine (1.0 g, 5.1 mmol). After 4 h at room temperature, the solvent was evaporated in vacuo, water added and the mixture stirred for 0.5 h. The resultant solid was collected by filtration, washed with water and hexane and dried in vacuo to give the ketohydrazine. A mixture of the ketohydrazine (0.80 g) and triethylamine hydrochloride (0.10 g, 0.73 mmol) in xylene (10 ml) was heated at reflux overnight. The solution was cooled to room temperature and the solvent removed in vacuo. The residue was chromatographed on silica gel, eluting with 5% methanol/dichloromethane, to give the title-phthalazine (0.21 g), 1H NMR (250 MHz, CDCl3) δ1.90-2.02 (4 H, m, 2 of CH2), 2.74-2.80 (2 H, m, CH2), 3.16-3.24 (2 H, m, CH2), 7.28 (1 H, m, Ar—H), 7.58 (1 H, t, J=1.7 Hz, Ar—H), 8.53 (1 H, m, Ar—H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe solvent removed in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-319007a64c074cc2b67fd129c6ab4380
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255305B1

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