1,3-Dichloro-2-nitrobenzene → 2-[4-(3-Chloro-2-nitroanilino)phenyl]ethanol

HRID 858425

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>O>[Cl:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2,6-dichloronitrobenzene (Norman, M. H.; Chen, N.; et al. PCT Int. Appl., WO 9940091 (1999)., Spada, A. P.; Fink, C. A.; Myers, M. R. PCT Int. Appl., WO 9205177 (1992)., 6.3 g, 32.8 mmol), 4-aminophenylethyl alcohol (4.9 g, 36 mmol) and sodium acetate (3.2 g, 39.3 mmol) was placed in a sealed tube and heated at 160° C. for 3 h. After cooling, the mixture was poured into water (100 mL) and extracted with ethyl acetate (300 mL). The organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL), then dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 4.57 g (72%) of the title compound as a red oil: 1H-NMR (CDCl3) δ 7.09–7.28 (6H, m), 6.91 (1H, dd, J=2.0, 7.1 Hz), 3.87 (2H, t, J=6.6 Hz), 2.86 (2H, t J=6.6 Hz).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate (300 mL)
washThe organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-28c23d5b2037450aa8d02bb33d48c492
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148234B2

Linked notes

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