3-Methoxypropylamine → HCID 62084770, compound

1-Chloro-2-fluoro-3-nitrobenzene (2.85 mmol, 0.500 g) was added to an oven dried 50 mL round-bottomed flask equipped for stifling under nitrogen. Dichlormethane (10 mL) and triethylamine (3.13 mmol, 0.437 mL) were added and the resultant solution was cooled to 0° C. with an ice-bath. 3-Methoxypropan-1-amine (2.85 mmol, 0.292 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 stirred for 16 hr. The reaction solution was poured into water and extracted twice with dichloromethane (50 mL). The organic layer was collected and water was subsequently removed with anhydrous Na2SO4 and the suspension was filtered. The filtrate was collected, concentrated, and dried in-vacuo affording an orange oil, which was then purified by chromatography on slica gel (10-70% ethyl aetate/hexanes) to afford 2-chloro-N-(3-methoxypropyl)-6-nitroaniline (30A) as a yellow solid (2.23 mmol, 0.542 g, 78% yield). ESI-MS: m/z 245.3 (M+H)+.

1. customdried 50 mL round-bottomed flask
2. customequipped
3. customThe ice-bath was removed
4. additionThe reaction solution was poured into water
5. extractionextracted twice with dichloromethane (50 mL)
6. customThe organic layer was collected
7. customwater was subsequently removed with anhydrous Na2SO4
8. filtrationthe suspension was filtered
9. customThe filtrate was collected
10. concentrationconcentrated
11. customdried in-vacuo
12. customaffording an orange oil, which
13. customwas then purified by chromatography on slica gel (10-70% ethyl aetate/hexanes)

ORD record

ord-ce6bf151442c4f2aa9fbbdd27e3ce40a

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138168B1