Aniline → 2-Chloro-6-nitro-N-phenylaniline

HRID 242834

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.[C:12]1([NH2:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-chloro-2-fluoro-3-nitrobenzene (983 mg, 5.60 mmol) in DMSO (3 mL) was purged with a stream of nitrogen prior to addition of phenylamine (1.0 mL, 11.2 mmol) and then stirred in a sealed tube at 100° C. for 3 h. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The organic layer was then washed with a saturated solution of KHSO4 (×3), then with water, followed by brine, dried (Na2SO4) and concentrated in vacuo affording (2-Chloro-6-nitrophenyl)phenylamine as a dark orange oil (1.35 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 8.15 (1H, s), 8.03 (1H, dd, J=8.40, 1.49 Hz), 7.63 (1H, d, J=7.90 Hz), 7.32-7.23 (2H, m), 7.08-6.99 (2H, m), 6.86 (2H, d, J=7.90 Hz).

Workup

temperatureAfter cooling to RT
customthe reaction mixture was partitioned between EtOAc and water
washThe organic layer was then washed with a saturated solution of KHSO4 (×3)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b433d264c3d343d1bf85b201933141df
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Linked notes

Loading…