4-Hydroxybenzaldehyde oxime

Step 1: Preparation of 4-hydroxy-benzaldehyde oxime; 4-Hydroxy-benzaldehyde (5 g, 40.94 mmol) was dissolved in EtOH (100 ml). Thereto, hydroxyl amine.HCl (4.3 g, 61.41 mmol) and pyridine (9.9 ml, 122.82 mmol) are added. The mixture is refluxed for 1 hour. The resultant is concentrated under a reduced pressure, extracted with EtTo a 100-ml flask, 500 mg (4.09 mmol) of 4-hydroxybenzaldehyde was added and dissolved in 10 ml of ethanol, followed by stirring. 1 ml (12.3 mmol, 3.0 eq) of pyridine and 427 mg (6.14 mmol, 1.5 eq) of hydroxylamine hydrochloridewere added thereto, and refluxed at 80°C under stirring for 1 hour. After completion of the reaction, the reaction productwas concentrated under reduced pressure and diluted with ethyl acetate (30 ml) and washed with water (70 ml). Afterseparation of layers, an organic layer was washed with a saturated NH4Cl aqueous solution, and then washed withwater. An organic layer was separated and washed with a NaCl aqueous solution, and then dehydrated and dried overMgSO4, and concentrated under reduced pressure to obtain 550 mg (98percent) of a title compound.1H NMR (dimethyl sulfoxide-d4, 600MHz) δ 10.83(s, 1H), 9.75(br, 1H), 7.99(s, 1H), 7.38(d, 2H), 6.75(d, 2H)Mass[M+H] : 138.05General procedure: Hydroxylamine hydrochloride (0.138 g, 2 mmol), ZnO nanotubes (0.071 g, 0.8 mmol), silica gel (0.43 g) and aldehyde (ketone) (1 mmol) were ground together in a mortar with a pestle at room temperature for a period of time as indicated in Tables 1 and 2. The progress of the reaction was monitored by TLC. After complete disappearance of the starting materials, the reaction mixture was poured with diethyl ether (2×10 mL) and filtered to remove silica gel and ZnO nanotubes, The filtrate mixed with water and extracted. The solvent was removed in vaccuo to give the product which was recrystallized from suitable solvent and afforded the TLC and 1H-NMR pure products in 75-98 percent isolated yields.NThe halogenated 4-hydroxybenzaldehydes Ib-Ih (FIG. 7) were either commercially available or prepared according to the procedure described in literature (Lawrence et al., 2003). The oκimes 2a-2h (FIG.7) were synthesized in excellent yields by condensation of hydroxylamine with the aldehydes Ia-Ih in basic alcoholic solvent. The final compounds 3a-3h (FIG. 7) were synthesized in good yields by condensation of oximes 2a-2h with cyclohexanecarboxylic acid chloride in dry dichloromethane in present of pyridine from 0 °C to room temperature overnight (Scheme 1) (See Supplemental Material below). Compound 4 and 5 were prepared as the similar method as the compound 3 (FIG. 8). The final compounds 3a-3h, 4 and 5 reported here were fully characterized by First step, p-hydroxybenzaldehyde (2.55 g) hydroxyamine hydrochloride (2.60 g) and NaOAc (3.40 g) were dissolved in EtOH (80 ml). The reaction mixture was stirred at room temperature for 6 h.EtOH was removed under reduced pressure. Hweigh precisely P-hydroxybenzaldehyde (2.55 g), hydroxylamine hydrochloride (2.60 g) and anhydrous sodium acetate (3.40 g), dissolve in ethanol (80 mL), stir at room temperature for 6 hours, Recover the solvent with the reaction solution, add water, mix thoroughly, dissolve, extract 40 ml ethyl acetate, extract a total of 3 times, recover solvent with phase of ethyl acetate, light yellow solid of2.66 g of p-hydroxyoxime are obtained.General procedure: A mixture of primary amine (1 mmol), THICA (5 molpercent), acetaldoxime(10 molpercent), and H

Molecular Weight:137.14
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:52.8
Heavy Atom Count:10
Complexity:117
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes