1-Chloro-2-nitrobenzene → N-(4-Methoxyphenyl)-2-nitroaniline

HRID 2180354Notes

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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[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

Conditions

Temperature: 100 °C

Procedure

Pd2(dba)3 (4.6 mg, 0.005 mmol, 1 mol % Pd), ligand 1 (see FIG. 1) (8.4 mg, 0.02 mmol) and NaOt-Bu (2 mg, 0.02 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 238 mg (98% 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-1c0bd9f9400346678f78b2147cf7f5f3
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06888029B2

Reaction notes

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