* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the American Chemical Society, 1966, vol. 88, # 14, p. 3318 - 3327
2
[ 10388-19-9 ]
[ 4481-28-1 ]
Yield
Reaction Conditions
Operation in experiment
87%
With triethylamine In water; ethyl acetate; acetonitrile
B. 3-Carboxybenzamide A mixture of 3-iodobenzamide (4.28 g, 17.3 mmol), water (25.00 g, 1387.7 mmol), triethylamine (8.00 g, 79.1 mmol), palladium(II) acetate (0.28 g, 1.2 mmol), and bis(diphenylphosphino)propane (0.52 g, 1.3 mmol) in acetonitrile (50 mL) was pressurized to 40 psi with carbon monoxide and the pressure was released. After six such cycles, the bottle was pressurized again and the contents were stirred at 85° C. for 3 h. The reaction mixture was cooled to room temperature and depressurized. The solvent was evaporated and ethyl acetate (200 mL) was added. The solution was filtered and then extracted with water (2*200 mL). The combined aqueous layers were acidified with 12 M HCl to pH 0. The solid was filtered off and air-dried to give 3-carboxybenzamide (1.93 g, 87percent) as a yellow solid
3-lodobenzoic acid (2.00 g, 8.06 mmol) was dissolved in THF (20 mL) then oxalyl chloride (1.4 mL, 16 mmol) and DMF (0.05 mL) were added and the resulting mixture stirred for 2 hours. The volatiles were evaporated under reduced pressure and the residue was dissolved in THF (20 mL) and concentrated aqueous ammonia (10 mL). After 60 minutes water (200 mL) was added and after a further 30 minutes the resulting precipitate was collected by filtration and air dried to give the title compound (1142) (1.97 g, 99% yield) as a white powder; H NMR (400 MHz, cVMeOH) delta 8.23 (t, J = 1.8 Hz, 1 H), 7.90 (ddd, J = 7.9, 1.7, 1.0 Hz, 1 H), 7.86 (ddd, J = 7.8, 1.7, 1.0 Hz, H), 7.24 (t, J = 7.8 Hz, 1 H). LCMS Method C rt 5.29 min, m/z 248.1 [M+H}
99%
3-lodobenzoic acid (2.00 g, 8.06 mrnol) was dissolved in THF (20 mL) then oxalyl chloride (1.4 mL, 16 mrnol) and DMF (0.05 mL) were added and the resulting mixture stirred for 2 hours. The volatiies were evaporated under reduced pressure and the residue was dissolved in THF (20 mL) and concentrated aqueous ammonia (10 mL). After 60 minutes water (200 mL) was added and after a further 30 minutes the resulting precipitate was collected by filtration and air dried to give the title compound (1142) (1.97 g, 99% yield) as a white powder; 1H NMR (400 MHz, oVMeOH) delta 8.23 (t, J = 1.8 Hz, 1 H), 7.90 (ddd, J = 7.9, 1.7, 1.0 Hz, 1 H), 7.86 (ddd, J = 7.8, 1.7, 1.0 Hz, 1 H), 7.24 (t, J = 7.8 Hz, 1 H). LCMS Method C: rt 5.29 min, m/z 248.1 [M+Hf .
With triethylamine;palladium diacetate; In water; ethyl acetate; acetonitrile;
B. 3-Carboxybenzamide A mixture of 3-iodobenzamide (4.28 g, 17.3 mmol), water (25.00 g, 1387.7 mmol), triethylamine (8.00 g, 79.1 mmol), palladium(II) acetate (0.28 g, 1.2 mmol), and bis(diphenylphosphino)propane (0.52 g, 1.3 mmol) in acetonitrile (50 mL) was pressurized to 40 psi with carbon monoxide and the pressure was released. After six such cycles, the bottle was pressurized again and the contents were stirred at 85 C. for 3 h. The reaction mixture was cooled to room temperature and depressurized. The solvent was evaporated and ethyl acetate (200 mL) was added. The solution was filtered and then extracted with water (2*200 mL). The combined aqueous layers were acidified with 12 M HCl to pH 0. The solid was filtered off and air-dried to give 3-carboxybenzamide (1.93 g, 87%) as a yellow solid
With cesium acetate In ISOPROPYLAMIDE at 20 - 130℃; for 20h; Inert atmosphere;
28
Reference Example 28 3-(6-Methoxy-1H-indol-2-yl)benzamide At room temperature, to a suspension of 6-methoxy-1H-indole (500 mg), palladium (II) acetate (76.1 mg) and cesium acetate (1.76 g) in N,N-dimethylacetamide (1.7 mL) was added 3-iodobenzamide (1.05 g), and the mixture was stirred at 130° C. for 20 hours under an argon gas atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The mixture was filtered through Celite (registered trademark) to remove the insoluble materials. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane-ethyl acetate-methanol). To the obtained crude product was added a mixed solvent of hexane-diisopropyl ether, and the suspension was stirred at room temperature for 15 minutes. The precipitate was collected by filtration, washed with the same mixed solvent, and then dried under reduced pressure to obtain the title compound (169 mg). Further, the structural formula and the spectral data of the title compound were shown in Table 70.
With hydroxylamine hydrochloride; caesium carbonate; In water; dimethyl sulfoxide; at 125℃; for 48h;
General procedure: Aldehyde (0.5mmol), NH2OH·HCl (0.6mmol) and Cs2CO3 (0.6mmol) were stirred at 125C for 48h in a 3:1 mixture of DMSO-H2O (2mL) under air. The progress of the reaction was monitored by TLC using ethyl acetate and hexane as eluent. After completion, the reaction mixture was cooled to room temperature and treated with water (1mL). The resulting mixture was extracted with ethyl acetate (3×5mL). Drying (Na2SO4) and evaporation of the solvent gave a residue that was purified on silica gel column chromatography using ethyl acetate and hexane. The purified products were identified by 1H NMR spectra and the melting points comparison with the literature data.
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