2-Nitroaniline → HCID 22478779, compound
Reaction equation
[N+:1]([C:4]1[CH:10]=CC=C[C:5]=1[NH2:6])([O-:3])=[O:2].C([C:15]1[CH:20]=[C:19](C)[CH:18]=[C:17](C(C)(C)C)[C:16]=1O)(C)(C)C.C(N(CC)CC)C.C(Cl)(=[O:37])C=C>CN(C1C=CN=CC=1)C.ClCCl>[N+:1]([C:4](=[CH2:10])[C:5]([NH:6][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:37])([O-:3])=[O:2]Participants
Procedure
To a mixture of 2-nitroaniline (1.73 g, 12.5 mmol), DMAP (321 mg, 2.6 mmol) and 2,6-di-tert-butyl-4-methylphenol (308 mg) in dry dichloromethane (50 mL) at 0° C. was added triethylamine (10.6 mL, 76 mmol) followed by acryloylchloride (3.2 mL, 38 mmol, 3.0 equiv.), and the mixture was stirred at room temperature for 16 h. The solution was diluted with dichloromethane (250 mL), cooled to 0° C. and the excess of reagent quenched with saturated NaHCO3 (stirring for 1 h). The organic layer was then washed (5% KHSO4, then brine), dried (MgSO4), filtered and concentrated under reduced pressure. After purification through chromatographic column on silica gel (elution 50% ether in hexanes), 642 mg (3.34 mmol, 27% yield) of the amide was obtained. 13C NMR (300 MHz, CDCl3) δ (ppm): 163.6, 136.0, 135.6, 134.5, 131.3, 128.6, 125.4, 123.1, 121.8. LRMS=193.2 (M+1).
Workup
- temperaturecooled to 0° C.
- customthe excess of reagent quenched with saturated NaHCO3 (stirring for 1 h)
- washThe organic layer was then washed (5% KHSO4
- dry with materialbrine), dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customAfter purification through chromatographic column on silica gel (elution 50% ether in hexanes)
Sources & evidence
- ORD record
- ord-b8e1d5edbc8b4458be7427a272b5b965
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868204B2
Reaction notes
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