Methylamine → N-(3-Chloro-4-nitrobenzylidene)methanamine

3-Chloro-4-nitrobenzaldehyde (251 mg 1.35 mmole) was dissolved in dichloromethane (2 mL) and methylamine, 2M in THF (0.88 mL, 1.76 mmole) was added along with 3A Sieves (400 mg). The reaction was stirred at room temperature for 18.5 hours. The sieves were filtered and washed with more dichloromethane. The filtrate was evaporated, however only partial conversion to the imine was observed. The residue was redissolved in dichloromethane (2 mL) and methylamine. 2M in THF (1.0 mL, 2.0 mmole) was added along with powdered 3A Sieves (400 mg). The reaction was stirred at room temperature for a further 16.5 hours. The sieves were filtered and washed and the filtrate evaporated to give the title compound as an oil which quickly crystallised (199 mg). 1H-NMR (CDCl3, 500 MHz): δ 3.60 (d, J=1.89 Hz, 3H), 7.73 (dd, J=1.89, 8.51 Hz, 1H), 7.93 (m, 2H), 8.30 (q, J=1.58 Hz, 1H).

1. filtrationThe sieves were filtered
2. washwashed with more dichloromethane
3. customThe filtrate was evaporated
4. dissolutionThe residue was redissolved in dichloromethane (2 mL)
5. stirringThe reaction was stirred at room temperature for a further 16.5 hours
6. filtrationThe sieves were filtered
7. washwashed
8. customthe filtrate evaporated

ORD record

ord-9eed2ddf3c1e468ea05a012db4af3811

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2