ChemicalBook CAS DataBase List 4-Aminoveratrole

4-Aminoveratrole synthesis

9synthesis methods

Product Name:4-Aminoveratrole
CAS Number:6315-89-5
Molecular formula:C8H11NO2
Molecular Weight:153.18

(1) Put 5000kg of methanol and 1250kg of 3,4-dimethoxynitrobenzene into the chemical kettle, and the subsequent feeding was carried out in accordance with the ratio, stirred well, pumped into the first-stage hydrogenation kettle, added 125kg of Pd/Al2O

709-09-1
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6315-89-5
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Yield:6315-89-5 93%

Reaction Conditions:

with hydrazine;palladium on activated charcoal in ethanol;water for 24 h;Heating / reflux;

Steps:

3 Synthesis of 4-amino-1,2-dimethoxybenzene (9)
4-Nitro-1,2-dimethoxybenzene (8) (1.03 g, 5.62 mmol) was dissolved in 95 % (v/v) ethanol (60 ml) and hydrogenated with hydrazine hydrate (30 ml) over palladium on charcoal (0.11 g). The reaction was refluxed for 24 hours. The hot solution was filtered through celite and solvent removed under reduced pressure. Water was added and the product was extracted into dichloromethane, dried over sodium sulfate, filtered and solvent removed under reduced pressure to give a viscous liquid, which was then placed on ice to give 0.80 g of (9) as a white powder (5.22 mmol, 93 % yield). Melting point: 82-85 C (Literature mp: 83-87 C). 30 Decomposition at: 205 C. 1H n. m. r. (300 MHz, CDCl3): δ 6.66 (d, 1 H, J 8.4 Hz, Ar-H); 6.26 (d, 1 H, J 2.6 Hz, Ar-H); 6.18 (dd, 1 H, J 8.4 Hz, 2.6 Hz, Ar-H); 3.77 (s, 3H, [C1]-OCH3), 3.76 (s, 3H, [C2]-OCH3), 3.38 (br s, 2H, NH2). 13C n. m. r. (75 MHz, CDCl3): δ 148.9, (C1); 141.1, (C2); 139.8, (C4); 112.3, (C6); 105.5, (C5); 99.8, (C3); 55.7, ( [C1]-OCH3); 54.7, ([C2]-OCH3). IR (Nujol): 3380, br s; 1596, m; 1514, s; 11463, s; 1236, s; 849, m. Mass spectrum (ESI, +ve): m/z 153.8 [M]+.

References:

Monash University WO2003/99762, 2003, A1 Location in patent:Page 24-25

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