Sodium Iodide → Methyl 2-(3-methoxypropylamino)-3-nitrobenzoate

Temperature

0 °C

Methyl 2-amino-3-nitrobenzoate (3.82 mmol, 0.75 g) in DMF (20 mL) was added NaI (8.40 mmol, 1.26 g). The reaction solution was stirred at 0° C. for 5 min and then added NaH (5.00 mmol, 0.20 g) at 0° C. The reaction solution was stirred at 0° C. for 30 min and then added 1-bromo-3-methoxypropane (5.00 mmol, 0.77 g). The reaction solution was heated to 80° C. and kept stirring at 80° C. for 6 hr. After cooling down the reaction solution was poured into H2O, extracted with EtOAc. The extract was washed with H2O, brine dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, EtOAc-hexane: 5:95) to afford methyl 2-(3-methoxypropylamino)-3-nitrobenzoate (44A) (1.49 mmol, 800 mg, yield: 78.1%). ESI-MS: m/z 269.3 (M+H)+.

1. customat 0° C
2. stirringThe reaction solution was stirred at 0° C. for 30 min
3. temperatureThe reaction solution was heated to 80° C.
4. stirringkept stirring at 80° C. for 6 hr
5. temperatureAfter cooling down the reaction solution
6. extractionextracted with EtOAc
7. washThe extract was washed with H2O, brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationThe filtrate was concentrated in vacuo
11. custompurified by flash chromatography (silica gel, EtOAc-hexane: 5:95)

ORD record

ord-d610d45c937d4f05a1fdc7a8ad1fe604

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138168B1