ChemicalBook CAS DataBase List 3-Amino-4-hydroxybenzoic acid

3-Amino-4-hydroxybenzoic acid synthesis

10synthesis methods

Product Name:3-Amino-4-hydroxybenzoic acid
CAS Number:1571-72-8
Molecular formula:C7H7NO3
Molecular Weight:153.14

616-82-0 Synthesis

616-82-0
225 suppliers
$10.00/5g

1571-72-8
260 suppliers
$8.00/1g

Yield:1571-72-8 98%

Reaction Conditions:

with hydrogenchloride;tin(ll) chloride at 0; for 1 h;Reflux;

Steps:

3-Amino-4-hydroxybenzoic acid (1)
To tin(II) chloride (207 mg, 1.09 mmol), 12N-HCl (1.5 mL) and 4-hydroxy-3-nitrobenzoic acid (100 mg, 0.55 mmol) were added successively at 0°C, and the reaction mixture was refluxed for 1 h. After addition of water, the reaction mixture was adjusted to pH 1 using 2N NaOH. The precipitates obtained were filtered and washed with water. The filtrate was concentrated in vacuo, and methanol was added to the residue. The formed precipitate was filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using methylene chloride and methanol (5:1) as eluent to obtain compound 1 (82 mg, 98%) as a brown solid [¹H NMR (500 MHz, DMSO-d₆) δ 11.30 (brs, 1 H), 9.42 (brs, 3 H), 7.79 (s, 1 H), 7.60 (d, 1 H, J = 8.0 Hz), 7.07 (d, 1 H, J = 8.0 Hz)].

References:

Kim, Min Jo;An, Hye Jin;Kim, Dae Hyun;Lee, Bonggi;Lee, Hye Jin;Ullah, Sultan;Kim, Su Jeong;Jeong, Hyoung Oh;Moon, Kyoung Mi;Lee, Eun Kyeong;Yang, Jungho;Akter, Jinia;Chun, Pusoon;Moon, Hyung Ryong;Chung, Hae Young [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 4,p. 684 - 688] Location in patent:supporting information

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