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Step A 5,6-Diaminonicotinic acid See Markwald, W. Chem. Ber. 1984, 27, 1317. To a stirred solution of SnCl2 (4.16 g, 22.0 mmol) in concentrated HCl (11 mL) at 0 C. was added in portions 5-nitro-6-aminonicotinic acid (1.01 g, 5.5 mmol). The resulting orange mixture was then heated to 100 C. under argon for 75 min. The mixture was then cooled to RT and was then placed in an ice bath and neutralized with concentrated aqueous ammonia (to pH 6-7), resulting in a thick cream-colored mixture. The mixture was then acidified to pH 4 with acetic acid and the precipitate collected by filtration, washed with H2O and dried under vacuum overnight to afford the title compound: 1H NMR (300 MHz, DMSO-d6): δ7.98 (d, J=2.1 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 6.24 (br s, 2H), 5.00 (br s, 2 H).
Step A 5,6-Diaminonicotinic Acid See Markwald, W. Chem. Ber. 1984, 27, 1317. To a stirred solution of SnCl2 (4.16 g, 22.0 mmol) in concentrated HCl (11 mL) at 0 C. was added in portions 5-nitro-6-aminonicotinic acid (1.01 g, 5.5 mmol). The resulting orange mixture was then heated to 100 C. under argon for 75 min. The mixture was then cooled to RT and was then placed in an ice bath and neutralized with concentrated aqueous ammonia (to pH 6-7), resulting in a thick cream-colored mixture. The mixture was then acidified to pH 4 with acetic acid and the precipitate collected by filtration, washed with H2O and dried under vacuum overnight to afford the title compound: 1H NMR (300 MHz, DMSO-d6): δ 7.98 (d, J=2.1 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 6.24 (br s, 2H), 5.00 (br s, 2H).
3
[ 267875-45-6 ]
[ 104685-76-9 ]
Yield
Reaction Conditions
Operation in experiment
With sodium carbonate; In methanol hydrochloride;
Step B Methyl-5,6-diaminonicotinate A solution of 5,6-diaminonicotinic acid (5.5 mmol) in saturated methanolic HCl was heated to reflux for 3 h. The yellow solution was cooled to RT and treated with solid sodium carbonate until basic (pH 9). The mixture was filtered through Celite and the filter cake was rinsed well with methanol. The filtrate was concentrated to an oily green solid. Silica gel chromatography (16:1:1 EtOAc-MeOH-NH4OH) afforded the title compound as a pale pink solid: Rf (8:1:1 EtOAc-MeOH-NH4OH)=0.54; 1H NMR (400 MHz, DMSO-d6): δ7.94 (d, J=2.0 Hz, 1H), 7.15 (d, J=2.0 Hz, 1H), 6.24 (s, 2H), 4.90 (s, 2H), 3.73 (s, 3H).
With sodium carbonate; In methanol hydrochloride;
Step B Methyl-5,6-diaminonicotinate A solution of 5,6-diaminonicotinic acid (5.5 mmol) in saturated methanolic HCl was heated to reflux for 3 h. The yellow solution was cooled to RT and treated with solid sodium carbonate until basic (pH 9). The mixture was filtered through Celite and the filter cake was rinsed well with methanol. The filtrate was concentrated to an oily green solid. Silica gel chromatography (16:1:1 EtOAc-MeOH-NH4OH) afforded the title compound as a pale pink solid: Rf(8:1:1 EtOAc-MeOH-NH4OH)=0.54; 1H NMR (400 MHz, DMSO-d6): δ 7.94 (d, J=2.0 Hz, 1H), 7.15 (d, J=2.0 Hz, 1H), 6.24 (s, 2H), 4.90 (s, 2H), 3.73 (s, 3H).
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