2-Iodo-6-methoxybenzoic acid synthesis
- Product Name:2-Iodo-6-methoxybenzoic acid
- CAS Number:66195-39-9
- Molecular formula:C8H7IO3
- Molecular Weight:278.04
53600-33-2
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Yield:66195-39-9 85%
Reaction Conditions:
Stage #1: 6-methoxyanthranilic acidwith hydrogenchloride;sodium nitrite in water;acetone at 0; for 0.5 h;
Stage #2: with potassium iodide in water;acetone at 90; for 6 h;
Steps:
4.5. The procedure for the synthesis of compound (11)
The 2-amino-6-methoxybenzoic acid 10 (2.0 g, 11.9 mmol) wasadded to the solution with ice water (28.0 mL), HCl (10 M, 7.2 mL) andacetone (10.0 mL). The suspension was cooled to 0 °C followed by theaddition of sodium nitrite (1.66 g, 24.0 mmol) in 12.0 mL of water. Thereaction was stirred for 30 min at 0 °C. Then KI (3.98 g, 24.0 mmol) wasadded to the solution. The reaction was heated to 90 °C for 6 h. Thereaction was cooled and quenched with saturated aqueous NH4Cl, andextracted with CH2Cl2. The combined extracts were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purifiedby silica gel chromatography. 4.5.1. 8-methoxy-3-methyl-1H-isochromen-1-one (11)White solid (yield: 85%); Rf=0.24 (CH2Cl2/EtOAc 1/1). 1H NMR(400 MHz, CDCl3) δ 12.17 (s, 1H), 11.35 (s, 1H), 7.41 (t, J=8.4 Hz,1H), 6.72 (d, J=8.5 Hz, 1H), 6.49 (d, J=8.3 Hz, 1H), 4.07 (s, 3H).ESI-MS (m/z):278.1 [M+H]+.
References:
Huang, Chao;Xiong, Juan;Guan, Hui-Da;Wang, Chang-Hong;Lei, Xinsheng;Hu, Jin-Feng [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 10,p. 2027 - 2040]
579-75-9
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38169-97-0
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5025-59-2
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