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ChemicalBook CAS DataBase List 2-Chloro-3-methoxyaniline

2-Chloro-3-methoxyaniline synthesis

3synthesis methods
-

Yield: 100%

Reaction Conditions:

with iron;acetic acid in ethanol for 3.5 h;Heating / reflux;

Steps:

3C.C Step C
2-Chloro-3-nitroanisole C3 (1.38 g; 7.36 MMOL) was dissolved in a mixture of glacial acetic acid (19 ML)/ETHANOI (19 mL). To this solution was added iron powder (1.64 g; 29.4 MMOL). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid NA2CO3 and the product extracted with CH2CI2 (3X 150 mL). The extracts were combined and washed with saturated. brine and then dried(NA2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline C4 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps. MS 157.9 (MH) + ; Homogeneity by HPLC (TFA) 220 nm: 86%.

References:

BOEHRINGER INGELHEIM INTERNATIONAL GMBH;BOEHRINGER INGELHEIM PHARMA GMBH & CO KG WO2004/103996, 2004, A1 Location in patent:Page 42-43

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