Hydrazine, [4-(phenylmethoxy)phenyl]-, hydrochloride (1:1)

Cream to brown fluffy powder

(4-(Benzyloxy)phenyl)hydrazine hydrochloride (2).; Note: The reaction mixture and all added solutions were maintained at 0 °C during this procedure. 4-Benzyloxyaniline hydrochloride (3.00 g, 12.5 mmol) was added to cone. aq. HC1 (25 mL) and stirred for 10 min at 0 °C, followed by dropwise addition of a solution of NaN0Note: The reaction mixture and all added solutions were maintainedat 0 C during this procedure. 4-Benzyloxyanilinehydrochloride (3) (3.0 g, 12.5 mmol) was added to concd aq HCl(25 mL) and stirred for 10 min at 0 C, followed by dropwise additionof NaNO2 (852 mg, 12.3 mmol) in water (6 mL) over the courseof 15 min. The mixture was stirred for additional 15 min and then asolution of SnCl2 (6.4 g, 33.1 mmol) in concd aq HCl (7.5 mL) wasadded dropwise. The reaction mixture was stirred for 1 h and filteredto yield an off-white precipitate, which was washed withwater and triturated with Et2O, to afford an off-white solid (2.9 g, 92percent); Mp 179–181 C. IR: mmax (KBr) cm1: 3232, 2907 (br), 1638, 1618, 1511, 1246, 1178. 1H NMR (DMSO-d6, 400 MHz) d 10.14(br s, 3H, NH–NH2), 7.35–7.48 (m, 4H, Ar-H), 7.27–7.35 (m, 1H, Ar-H), 6.92–7.05 (m, 4H, Ar-H), 5.06 (s, 2H, CH2). 13C NMR(DMSO-d6, 100 MHz) d 153.7 (ArC–O), 139.1 (ArC–N), 137.3(ArC), 128.5 (ArC), 128.4 (ArC), 128.3 (ArC), 127.9 (ArC), 127.7(ArC), 117.1 (ArC), 116.9 (ArC), 115.5 (ArC), 115.3 (ArC), 69.5(CH2). HRMS (EI): Found 215.1180 (M+H)+, C13H15N2O requires215.1184.(a) A. A. (b) 5-Benzyloxytryptophole 4-Benzyloxyphenylhydrazine hydrochloride (340 g, 1.35 mol) is added to methanol (8.3), and dihydrofuran (162 ml, ca. 2.14 mol) is added thereto, followed by stirring at 50 °C for 10 hours while suspending. The solvent is distilled off under reduced pressure, and chloroform (3) is added thereto. The insoluble matters are filtered off, and the filtrate is concentrated to give an oily substance which is then purified by silica gel column chromatography (developing solvent; CHCL9: AcOEt:MeOH=80:40:1 - 40:40:1) to give 170 g of an oily substanceExample 7Synthesis of Indomethacin DerivativesCompound 31 has been reported by Yoriko Iwata, et al. J. Med. Chem. (2001), 44, 1718-1728 and is readily synthesized from the commercially available hydrazine 28 through the Fisher indole synthesis with levulinic acid. Alkylation of 31 with tBocNH(CH2)4Br and deprotection of the tBOC amine and the tBu-ester leads to amino acid 33 which can be reacted with NHS'S-Acetyl-MAG3 following the procedure in: Wang Y, et al. Nat Protoc. 2007; 2(4), 972-8 to afford 34. The reagent S-Acetyl-MAG3-NHS ester is available commercially (KeraFAST Inc., Boston, Mass., USA; catalog no. ES1001; see the supplier web site: www.kerafast.com/p-1447-s-acetyl-mag3-nhs-ester.aspx'gclid=Cj0KEQjwur2eBRDtvMS0gIuS-dYBEiQANBPMR3SKY-ABw0HCC08Gud53dB29wsldYYUl3UeQFvVxc_gaAiIA8P8HAQ; see also Winnard P. et al., Nucl. Med. Biol. (1997), 24(5): 425-32; Wang Y. et al., Nat. Protoc. (2007), 2(4): 972-8; Rusckowski M. et al., Cancer Biotherapy & Radiopharmaceuticals (2007), 22(4): 564-72; and Wang Y. et al., European J. Nucl. Med. Mol. Imag. (2009), 36(12): 1977-86).Weigh 500 mg of

Molecular Weight:250.72
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:250.0872908
Monoisotopic Mass:250.0872908
Topological Polar Surface Area:47.3
Heavy Atom Count:17
Complexity:184
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes