Stannous Chloride → 2-Methoxy-4-morpholinoaniline

Temperature

70 °C

To a solution of 4-(3-methoxy-4-nitrophenyl)morpholine (Preparation 78, 1.00 g, 4.20 mmol) in EtOH (42 mL) was added tin (II) chloride (2.79 g, 14.69 mmol). The reaction mixture was heated to 70° C. for 18 hours. The reaction mixture was diluted with ice-water (10 mL) and concentrated in vacuo. Aqueous Na2CO3 (2M, 20 mL) was added and the reaction mixture was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by passage through a SCX-2 cartridge eluting with 100% MeOH—1M NH3 in MeOH to give the title compound (418 mg, 48%).

1. concentrationconcentrated in vacuo
2. additionAqueous Na2CO3 (2M, 20 mL) was added
3. extractionthe reaction mixture was extracted with EtOAc (3×20 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by passage through a SCX-2 cartridge
8. washeluting with 100% MeOH—1M NH3 in MeOH

ORD record

ord-26f580a1c791464387c9f16f60de5d35

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409907B2