4-Hydroxy-3-nitrophenylacetic acid

yellow crystalline powder

(4-hydroxy-3-nitrophenyl)acetic acid is a monocarboxylic acid that is acetic acid carrying a 2-hydroxy-3-nitrophenyl substituent at C-2. It has a role as a hapten. It is a conjugate acid of a (4-hydroxy-3-nitrophenyl)acetate.

4-Hydroxyphenylacetic acid 1 (31 g; 203.7 mmol) was dissolved in acetic acid (186 mL) and cooled to 5 Celsius on ice bath. Nitric acid (62 mL of 50-70percent) was added dropwise to a solution of 4-hydroxyphenylacetic acid for 40 min. and the reaction mixture was held at that temperature for 15 min. The reaction mixture was added into 600 mL of water and filtered precipitate, washed with water, dried. MW CIn a first step, carried out according to Humel in Synth. Commun. 15, pages 1081-88 (1985), to a magnetically stirred solution of 100 g (0.65, mole) of 4-hydroxyphenyl acetic acid in 250 ml of glacial acetic acid was added dropwise a mixture of 40 ml of nitric acid (1.4 specific gravity) and 60 ml glacial acetic acid. General procedure: An appropriate phenol compound 8a–13a (1 mmol) was mixed with 60percent HNO3 (4.8 mmol). Theresulting suspension was stirred at room temperature for 10 min for 8a and 9a, for 30 min for 10a, 12aand 13a, or overnight for 11a, leading eventually to an intensively dark red solution. HPLC analysisconfirmed the absence of starting material and the presence of 3 major products corresponding mostlikely to nitro derivatives resulting from nitration at the o- and p-positions of the hydroxy group fromthe m-substituted phenols 8a, 10a and 12a, but only one product from the p-substituted phenols 9a, 11a and 13a. The crude nitrophenol 8b or 9b was diluted with water (20 mL) and applied onto aDowex 50W-X2 (200–400 mesh) column (1.5 cm × 6 cm, H+ form, equilibrated with water).The column was washed with water (100 mL) and then the product was eluted with 2 M HCl(20 mL/fraction). Fractions containing the target compound were combined and evaporated to drynessto give a yellow powder. After the nitration of phenols 10a, 12a and 13a, the reaction mixture (10b, 12b and 13b) was diluted with H2O (20 mL) and extracted with ethyl acetate (2 × 100 mL). Thecombined organic extract was washed with water (2 × 50 mL), dried with Na2SO4 and evaporatedunder reduced pressure. The nitration of 11a afforded 11b as an orange powder in the reaction mixture.After the filtration, the powder was washed with water and dried under reduced pressure to give a darkred powder 11b.(a) The solution of (4-hydroxyphenyl)acetic acid (4.65 g, 300 mmol) in glacial acetic acid (366 mL) was cooled to 10-15 °C, and nitric acid (100.5 mL, 65 w/wpercent) was added dropwise over a period of 1 hour. A precipitate was formed, and the mixture was stirred for 90 min at 10- 15 °C. Cold water (1100 mL) was added and stirred for 1 hour at 10-15 °C. The precipitate was filtered, washed with cold water (5x30 mL), and dried. 1-(4-Hydroxy-3-nitrophenyl)acetic acid was obtained (36.1 g, 62percent), mp: 145-150 °C.The solution of (4-hydroxyphenyl)acetic acid (4.65 g, 300 mmol) in glacial acetic acid (366 mL) was cooled to 10-15°C, and nitric acid (100.5 mL, 65 w/w percent) was added dropwise over a period of 1 hour A precipitate was formed and the mixture was stirred for 90 min at 10-15°C. Cold water (1100 mL) was added and stirred for 1 hour at 10-15°C. The precipitate was filtered, washed with cold water (5 x 30 mL) and dried. 1-(4-hydroxy-3-nitrophenyl)acetic acid was obtained (36.1 g, 62percent); mp: 145-150°CΞ;2-(2-(3, 5-dimethylisoxazol-4-yl)benzo[a) 2-(4-hydroxy-3-nitrophenyl)acetic acidTo a solution of 2-(4-hydroxyphenyl)acetic acid (10 g, 65.7 mmol) in AcOH (100 mL) at 0 °C was added concentrated HNO

A metabolite of Nitrotyrosine (N597000), which is excreted in the urine.

Molecular Weight:197.14
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:197.03242232
Monoisotopic Mass:197.03242232
Topological Polar Surface Area:103
Heavy Atom Count:14
Complexity:236
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes