3-Methoxypropylamine → HCID 21478623, compound

Temperature

0 °C

4-Chloro-2-fluoro-1-nitrobenzene (2.85 mmol, 0.500 g) was added to an oven dried 25 mL round-bottomed flask equipped for stirring under nitrogen. DMF (5 mL) was added and the resultant solution was cooled to 0° C. with an ice-bath. 3-Methoxypropan-1-amine (2.99 mmol, 0.306 mL) was then added drop-wise via syringe and the resultant solution was stirred at 0° C. for 1 hr. The ice-bath was removed and the reaction was allowed to warm to room temperature and stir for 16 hr. The reaction solution was then poured into water, extracted with ethyl acetate, and washed once with saturated aqueous sodium chloride. The organic layer was collected and subsequently dried with anhydrous Na2SO4 and filtered; filtrate was collected, concentrated, and dried in-vacuo affording 5-chloro-N-(3-methoxypropyl)-2-nitroaniline (32A) as an orange oil. This material was used directly in the next step without further purification. ESI-MS: m/z 245.3 (M+H)+.

1. customdried 25 mL round-bottomed flask
2. customequipped
3. additionDMF (5 mL) was added
4. customThe ice-bath was removed
5. temperatureto warm to room temperature
6. stirringstir for 16 hr
7. additionThe reaction solution was then poured into water
8. extractionextracted with ethyl acetate
9. washwashed once with saturated aqueous sodium chloride
10. customThe organic layer was collected
11. dry with materialsubsequently dried with anhydrous Na2SO4
12. filtrationfiltered
13. customfiltrate was collected
14. concentrationconcentrated
15. customdried in-vacuo

ORD record

ord-2a0491b04a554feea6de59fe2db19cd4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138168B1