2-Naphthylamine → HCID 15118556, compound

Temperature

90 °C

A mixture of 2-napthylamine (compound I, FIG. 3B) (1.43 g, 10 mmol), ethyl iodoacetate (2.14 g, 10 mmol), and sodium acetate (1.64 g, 20 mmol, dissolved in 2 ml of water) was stirred at 90° C. for 3 hours. The solid material obtained upon cooling was filtered and recrystallized from hexane to yield 1.5 g ethyl N-(2-naphthalenyl)glycinate (compound II, FIG. 3B) (yield, 65%, mp 83-84° C.) (Ramamurthy and Bhatt, J. Med. Chem. 32:2421-2426, 1989). A solution of above product (2.29 g, 10 mmol) in ethanol (10 ml) was refluxed with hydrazine hydrate (0.6 g, 12 mmol) for 10 hours. Solvent and excess reagent were distilled under vacuum. The product was recrystallized from ethanol to yield 1.8 g of N-(2-naphthalenyl)glycine hydrazide (compound III, FIG. 3B) (yield 82%, mp 147-148° C.). A mixture of compound III (2.15 g, 10 mmol) and 3,5-dibromo-2,4-dihydroxybenzaldehyde (3 g, 10 mmol) in ethanol (5 ml) was refluxed for 3 hours. The hydrazone that crystallized upon cooling was filtered, washed with ethanol, and recrystallized from ethanol to give 3.8 g (78%) of GlyH-101. Melting point (mp)>300° C., ms (ES−): M/Z 492 (M−); 1H nmr (DMSO-d6): δ 4.1 (s, 2H, CH2), 6.5-7.5 (m, 9H, aromatic, NH), 8.5 (s, 1H, CH═N), 10.4 (s, 1H, NH—CO), 11.9 (s, 1H, OH), 12.7 (s, 1H, OH). Compounds GlyH-102-109, GlyH-114-127 and AceH401-404 were synthesized similarly by condensing appropriate hydrazides with substituted benzaldehydes.

1. customThe solid material obtained
2. temperatureupon cooling
3. filtrationwas filtered
4. customrecrystallized from hexane

ORD record

ord-c4e27f095dc84dad98b21b50dc8e44fa

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414037B2