Identification | Back Directory | [Name]
4-(4-Chloro-benzyl)-2H-phthalazin-1-one | [CAS]
53242-88-9 | [Synonyms]
phthalazin-1(2H) 4-(4-Chlorobenzyl) Azelastine USP RC D Azelastine EP Impurity D Azelastine Impurity D(USP) Azelastine Related CoMpound D Phthalazinone Azelastine Analog 4-(4-Chlorobenzyl)phthalazin-1(2H)- Azelastine Hydrochloride EP Impurity D 4-(4-Chlorobenzyl)phthalazin-1(2H)-one 4-(4-Chlorobenzyl)-1(2H)-phthalazinone 4-(4-chloro-benzyl)-2h-phthalazin-1-one 4-[(4-chlorophenyl)methyl]phthalazin-1(2h)-one 4-[(4-Chlorophenyl)methyl]-1(2H)-phthalazinone 4-(4-Chlorobenzyl)-1,2-dihydrophthalazine-1-one 1(2H)-Phthalazinone, 4-[(4-chlorophenyl)methyl]- Azelastine Related Compound D (4-(4-chlorobenzyl)phthalazin-1(2H)-one) (1046191) | [EINECS(EC#)]
258-445-3 | [Molecular Formula]
C15H11ClN2O | [MDL Number]
MFCD02168779 | [MOL File]
53242-88-9.mol | [Molecular Weight]
270.71 |
Chemical Properties | Back Directory | [Melting point ]
206-207 °C(Solv: ethanol (64-17-5)) | [density ]
1.32±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
12.08±0.40(Predicted) | [color ]
White to Off-White |
Hazard Information | Back Directory | [Uses]
Stilbene-related heterocyclic compound with anti-HIV activity. A potent vasorelaxant agent. | [Synthesis]
The general procedure for the synthesis of 4-(4-chlorobenzylidene)-1-(2H)-phthalazinone from (E)-3-(4-chlorobenzylidene)isobenzofuran-1(3H)-one was as follows: intermediate 77 (Stage 2) 4-{[4-chlorobenzylidene]methyl}-1(2H)-phthalazinone (3 lb.) was combined with 3-[(4-chlorophenyl)methyl]-2-benzofuran-1(3H)-one (as prepared in Step 1) (10 equiv., corrected for loss on drying) were suspended in ethanol (37 vol.) and heated to about 85 °C under slight reflux. Subsequently, a mixture of a commercially available hydrazine hydrate solution (e.g., 12 eq. from Aldrich) with ethanol (0.63 vol.) was slowly added through a dropping funnel over a period of 1 hour. After the addition was complete, ethanol (0.63 volume) was added again through the dropping funnel. To remove traces of hydrazine hydrate, the reaction suspension was heated at ~85°C for 14 hours at slight reflux. Upon completion of the reaction, it was cooled to about 20 °C and sampled to check the conversion (HPLC showed 99% conversion). Next, acetone (0.35 v/v) was added to the reaction mixture over 30 minutes (note the exothermic reaction). The quenched suspension was stirred for at least 1 hour and then cooled to about 2°C at 30°C. After continued stirring at about 2 °C for 1 h, the product was isolated by filtration through a suction filter and washed with cold ethanol (about 0-5 °C, 3 x 10.9 v/v). The resulting light brown solid was completely dried on a vacuum suction filter protected by nitrogen to give 4-(4-chlorobenzyl)-1-(2H)-phthalazinone in 90-95% yield (corrected by 1H NMR measurements).1H NMR (400 MHz, DMSO-d6) data: δ 4.30 (s, 2H), 7.35 (m, 4H), 7.88 (m, 3H). 8.26 (d, 1H), 12.62 (s, 1H). | [References]
[1] Patent: WO2007/122156, 2007, A1. Location in patent: Page/Page column 114-115 |
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