Stannous chloride dihydrate → HCID 43132688, compound

Temperature

40 °C

N-Ethyl-3-nitro-N-phenylaniline (400 mg, 1.65 mmol) was dissolved in acetic acid (5 ml) at 40° C. followed by slow addition of tin (II) chloride dihydrate (1.50 g, 6.60 mmol). The reaction mixture was stirred at 40° C. for 2 hours and then for a further 2 hours at 75° C. The mixture was concentrated in vacuo and the obtained residue was diluted with ether (10 ml). Aqueous sodium hydroxide solution (2 ml) was added dropwise to the cooled (0° C.) solution. A solid formed was separated by filtration and was rinsed twice with hot ethyl acetate (25 ml). The filtrate was concentrated to approximately 30 ml and washed with 1 N sodium hydroxide, brine, dried over sodium sulfate and concentrated in vacuo to give N-ethyl-N-phenylbenzene-1,3-diamine as a yellow oil (117 mg, 1.04 mmol, 63% yield). 1H NMR (400 MHz, CDCl3): 6.87-7.28 (m, 7H), 6.28-6.83 (m, 2H), 3.74 (q, 2H), 3.59 (s, 2H), 1.20 (t, 3H); MS (EI) for C14H16N2: 212 (MH+).

1. waitfor a further 2 hours at 75° C
2. concentrationThe mixture was concentrated in vacuo
3. additionthe obtained residue was diluted with ether (10 ml)
4. additionAqueous sodium hydroxide solution (2 ml) was added dropwise to the
5. temperaturecooled (0° C.) solution
6. customA solid formed
7. customwas separated by filtration
8. washwas rinsed twice with hot ethyl acetate (25 ml)
9. concentrationThe filtrate was concentrated to approximately 30 ml
10. washwashed with 1 N sodium hydroxide, brine
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated in vacuo

ORD record

ord-f7a43f927ee44451887affb2f3140db1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697737B2