Water → Methyl 5-chloro-2-[(5-nitropyridin-2-yl)oxy]benzoate

HRID 1293263Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 5-chloro-2-hydroxybenzoate (2.35 g, 12.6 mmol), 2-chloro-5-nitropyridine (2.00 g, 12.6 mmol), and potassium carbonate (5.23 g, 37.8 mmol) in N,N-dimethylformamide (50 mL) was stirred at 120° C. for 1 h. The reaction mixture was poured into water and the aqueous mixture was extracted with a mixture (3/1) of ethyl acetate and toluene. The organic extracts were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1) to afford 3.79 g (97%) of the title compound: 1H-NMR (CDCl3) δ 8.94 (1H, d, J=2.8 Hz), 8.52 (1H, dd, J=9.0, 2.8 Hz), 8.05 (1H, d, J=2.8 Hz), 7.60 (1H, dd, J=8.6, 2.8 Hz), 7.18 (1H, d, J=8.6 Hz), 7.14 (1H, d, J=9.0 Hz), 3.73 (3H, s).

Workup

extractionthe aqueous mixture was extracted with a mixture (3/1) of ethyl acetate and toluene
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified
customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record: ord-a752656d7886463cbb336d2b117cc078
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238714B2

Reaction notes

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