ChemicalBook CAS DataBase List 5-Chloro-2-methoxyaniline

5-Chloro-2-methoxyaniline synthesis

7synthesis methods

Product Name:5-Chloro-2-methoxyaniline
CAS Number:95-03-4
Molecular formula:C7H8ClNO
Molecular Weight:157.6

4-Chloro-1-methoxy-2-nitrobenzene reduction.

89-21-4 Synthesis

89-21-4
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$12.00/5g

95-03-4
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$13.00/25g

Yield:95-03-4 98%

Reaction Conditions:

with iron(III) chloride;pyrographite;hydrazine hydrate in methanol for 16 h;Reflux;

Steps:

Intermediate s: 5-Chloro-2-methoxyaniline
Intermediate s: 5-Chloro-2-methoxyaniline Hydrazine hydrate (80%, 186 g, 2.975 mol) was added drop-wise to a refluxing mixture of 4-chloro-1-methoxy-2-nitrobenzene (Intermediate 4, 93 g, 0.496 mol), iron trichloride (9.3 g, 10% wt) and active carbon (9.3 g, 10% wt) in methanol (1 L). After the addition, the reaction mixture was stirred at reflux for 16 h, the reaction mixture was filtered and the solvent evaporated from the filtrate under vacuum. The residue was washed with petroleum ether (2 L) to give 5-chloro-2-methoxyaniline as a white solid (76.7 g, 98%). ¹H NMR (300MHz, CDCI₃) δ 6.67-6.65 (m, 3H), 3.83 (bs, 2H), 3.81 (s, 3H).

References:

GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED;BOUILLOT, Anne Marie Jeanne;MIRGUET, Olivier;LIDDLE, John;WALKER, Ann, Louise WO2015/91647, 2015, A1 Location in patent:Page/Page column 41

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60468-21-5 Synthesis