1-Chloro-2-nitrobenzene → N-(4-Methoxyphenyl)-2-nitroaniline
Reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Cl)([O-:11])=[O:10].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1>COCCOC.CCOCC.CCCCCCCCCCCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC([O-])(C)C.[Na+]>[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)([O-:11])=[O:10]Participants
9
Reactant 3
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 100 °C
Procedure
Pd(dba)2 (5.8 mg, 0.01 mmol, 1 mol % Pd), ligand 2 (see FIG. 1) (4.2 mg, 0.01 mmol) and NaOt-Bu (1 mg, 0.01 mmol) were stirred in 1 mL DME (anhy). After 10 minutes, the solution was added to a test tube containing (under an Argon atmosphere) K3PO4 (297 mg, 1.4 mmol), 2-nitrochlorobenzene (158 mg, 1.0 mmol), and p-anisidine (148 mg, 1.2 mmol). The test tube was capped and heated at 100° C. for 35 hours. The reaction mixture was cooled to r.t., diluted with ether and dodecane was added as an internal standard. The reaction mixture was purified by column chromatography (10% EtOAc/hexanes) to yield 234 mg (96% yield) of the product.
Workup
- additionthe solution was added to a test tube
- customThe test tube was capped
- temperatureThe reaction mixture was cooled to r.t.
- additionwas added as an internal standard
- customThe reaction mixture was purified by column chromatography (10% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-14a8a2cd95024fb89dbc876be5d2f13f
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06888029B2
Reaction notes
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