反应详情

温度

0 °C

An ice cold solution of Red-Al (65% in toluene) (3.55 ml, 11.63 mmol) in tetrahydrofuran (THF) (3.3 ml) was treated dropwise with a solution of 3-ethyl 5-methyl 2-amino-6-methyl-4-(p-tolyl)pyridine-3,5-dicarboxylate (1.91 g, 5.82 mmol) in tetrahydrofuran (THF) (23 ml). After stirring for 1 hour at 0° C., the reaction was quenched with water slowly, then diluted with EtOAc (10 mL) and 20% aq. NaOH (2 mL). The mixture was stirred for 20 min at rt, filtered, extracted with EtOAc, washed with brine, dried with Na2SO4, filtered, and concentrated to afford crude methyl 6-amino-5-(hydroxymethyl)-2-methyl-4-(p-tolyl)nicotinate (1.4679 g, 5.13 mmol, 88% yield) as brown solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.19 (d, J=7.8 Hz, 2 H), 7.03 (d, J=8.0 Hz, 2 H), 5.25 (s, 2 H), 4.42 (s, 2 H), 3.43 (s, 3 H), 2.42 (s, 3 H), 2.38 (s, 3 H); LCMS (m/z) ES+=287 (M+1).

1. customthe reaction was quenched with water slowly
2. additiondiluted with EtOAc (10 mL) and 20% aq. NaOH (2 mL)
3. stirringThe mixture was stirred for 20 min at rt
4. filtrationfiltered
5. extractionextracted with EtOAc
6. washwashed with brine
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated