反应详情

温度

75 °C

Methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate (0.74 g, 2.47 mmol) was dissolved in acetic acid (9 mL) at 45° C. and tin (II) chloride dihydrate (2.22 g, 9.84 mmol) was added. The mixture was stirred at 75° C. for 7 h and then was concentrated in vacuo. The residue was transferred to an Erlenmeyer flask using a little ethyl acetate and diluted with ether (20 mL). The mixture was stirred while cooling in an ice-water bath and sodium hydroxide (50% solution in water) (6 mL) was added dropwise. The solid which formed was removed by filtration and was washed with hot ethyl acetate. The combined filtrate was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate as a yellow solid (0.245 g, 0.907 mmol, 37% yield). 1H NMR (400 MHz, d6-DMSO): 7.87 (dd, 1H), 7.65 (td, 1H), 7.57 (td, 1H), 7.32 (dd, 1H), 6.93 (d, 1H), 6.66 (dd, 1H), 6.44 (d, 1H), 5.49 (s, 2H), 4.69 (s, 2H), 3.57 (s, 3H); MS (EI) for C15H14N2O3: 293 (MNa+).

1. concentrationwas concentrated in vacuo
2. additiondiluted with ether (20 mL)
3. stirringThe mixture was stirred
4. temperaturewhile cooling in an ice-water bath
5. additionsodium hydroxide (50% solution in water) (6 mL) was added dropwise
6. customThe solid which formed
7. customwas removed by filtration
8. washwas washed with hot ethyl acetate
9. concentrationThe combined filtrate was concentrated in vacuo
10. customthe residue was partitioned between ethyl acetate and water
11. washThe organic portion was washed with brine
12. dry with materialdried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vacuo