Dimethylformamide → 3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

HRID 1426165Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13](Cl)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32].CN(C=O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13]([O:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Cl:25])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(benzyloxy)-5-chloro-2-nitropyridine (1.00 g, 3.78 mmol), potassium carbonate (2.09 g, 15.1 mmol), 2-chlorophenol (1.46 g, 11.3 mmol) and DMF (16 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled, partitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL). The organic layer was washed with 2N NaOH (30 mL), water, and brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.73 g, 54.2% yield) as a light yellow solid. 1H NMR (CDCl3) δ 5.16 (s, 2H), 6.90 (s, 1H), 7.09 (d, 1H), 7.28-7.37 (m, 7H), 7.52 (d, 1H), 7.72 (s, 1H).

Workup

temperatureThe reaction mixture was cooled
custompartitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL)
washThe organic layer was washed with 2N NaOH (30 mL), water, and brine
customdried
concentrationconcentrated
customThe residue was purified by MPLC (Biotage)
washeluting with 5:1 hexane

Sources & evidence

ORD record: ord-27019af157bc4f0d8690ad89af05e1d3
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933077B2

Reaction notes

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