Ammonium Chloride → 6-Amino-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

To a stirred suspension of 1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 2, 1.04 g, 5.05 mmol) in EtOH (10 mL) and water (5 mL) is added ammonium chloride (2.70 g, 10.0 equiv.). To this mixture is added iron powder (0.85 g, 3.0 equiv.) in 3 portions. The resulting mixture is heated at reflux for 2 h and then is cooled to room temperature. The resulting mixture is filtered through celite and the filtrate is further diluted with water (100 mL). The filtrate is extracted with ethyl acetate (2×50 mL) and washed with saline (100 mL). The organic layers are combined, dried over MgSO4 and concentrated under reduced pressure to yield the title compound as a yellow solid (0.86 g, 97%), MS (m/z): 177.5 [M+H]+.

1. temperatureThe resulting mixture is heated
2. temperatureat reflux for 2 h
3. filtrationThe resulting mixture is filtered through celite
4. additionthe filtrate is further diluted with water (100 mL)
5. extractionThe filtrate is extracted with ethyl acetate (2×50 mL)
6. washwashed with saline (100 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-848ab0b7141c4c7cbc5fedb6d1aedd26

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645781B2