1,3-Benzodioxole-5-carboxylicacid, 6-amino-, methyl ester synthesis

6synthesis methods

Product Name:1,3-Benzodioxole-5-carboxylicacid, 6-amino-, methyl ester
CAS Number:40680-63-5
Molecular formula:C9H9NO4
Molecular Weight:195.1721

6-Nitro-1,3-benzodioxole-5-carboxylic acid methyl ester

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1,3-Benzodioxole-5-carboxylicacid, 6-amino-, methyl ester

40680-63-5
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Yield:40680-63-5 90%

Reaction Conditions:

with Pd/C;hydrogen in methanol;ethyl acetate at 50; for 12 h;

Steps:

3

Step 3: A mixture of methyl 6-nitrobenzo[d][l,3]dioxole-5-carboxylate (19.3 g, 85.7 mmol) and Pd/C (10%, 1.9 g) in ethyl acetate/methanol (200 mL/100 mL) was stirred at 50 °C under hydrogen atmosphere (hydrogen balloon) for 12 h. After this time, the Pd/C was removed through celite and washed with methanol. The combined filtrate was concentrated under reduced pressure to afford methyl 6-aminobenzo[d][l,3]dioxole-5-carboxylate as an off-white solid (15 g, 90%). LC/MS (ES⁺) calcd for C₉H₉N0₄: 195.1; found: 196.1 [M+H]. 1H NMR (400 MHz, DMSO-i d) d 7.07 (s, 1H), 6.66 (s, 2H), 6.35 (s, 1H), 5.93 (s, 2H), 3.72 (s, 3H).

References:

WO2020/33782,2020,A1 Location in patent:Paragraph 0268

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712-97-0 Synthesis