4-Iodo-3-methoxybenzenecarboxylic acid synthesis
- Product Name:4-Iodo-3-methoxybenzenecarboxylic acid
- CAS Number:282087-44-9
- Molecular formula:C8H7IO3
- Molecular Weight:278.04
2486-69-3
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282087-44-9
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Yield: 46%
Reaction Conditions:
Stage #1:3-methoxy-4-aminobenzoic acid with hydrogenchloride;sodium nitrite in water at 0;
Stage #2: with potassium iodide in water for 3 h;
Steps:
R
To a solution of 4-amino-3-methoxybenzoic acid (5 mg, 29.9 mmol) in H2O (30 mL) and HCI 37% (30 mL) at 0 0C, a solution of NaNO2 (2.27 g, 32.9 mmol) in H2O (10 mL) was slowly added. The solution obtained was then stirred for 20 minutes and then added at 0 0C to a solutionn of Kl (34.75 g, 7 mmol) in H2O (1OmL). The mixture was stirred for 3 hours. After cooling in an ice-water bath, the solid was filtered off. The filtrate was diluted with ethyl acetate, washed with 10% sodium methabisulphite, dried over anhydrous Na2SU4and concentrated to give 3.7 g of the title compound (46% yield).1H NMR (400 MHz, DMSO-d6) δ ppm: 3.90 (s, 3 H) 7.31 (dd, J 1.71 Hz and J 8.05 Hz, 1 H), 7.43 (d, J 1.71 Hz, 1 H), 7.92 (d, J 8.05 Hz, 1 H), 13.15 (b.s., 1H).
References:
NERVIANO MEDICAL SCIENCES S.R.L.;CALDARELLI, Marina;NUVOLONI, Stefano;QUARTIERI, Francesca WO2010/108921, 2010, A1 Location in patent:Page/Page column 44
35387-92-9
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586-38-9
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58123-77-6
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1000210-73-0
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