Water → 2-(2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-5-nitropyridine

HRID 31218Notes

Reaction equation

HRID 31218 reaction equation
[C:1]1([CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]1([CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([O:17][C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=4)=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 179785732,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-ol

Product 1

HCID 179785012-(2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-dihydro-2-phenyl-benzo[1,4]dioxin-6-ol (80 mg), 2-chloro-5-nitropyridine (56 mg) and potassium carbonate (52 mg) in dimethylformamide (1.0 ml) was stirred at 120° C. for 2 hrs. After cooling the mixture water (10 ml) was added and the precipitated product was filtered, washed with water and 2-propanol and dried under reduced pressure. Yield is 60 mg and mp 163-170° C. 1H NMR (DMSO-d6) δ=4.16 (dd, J=8.5, 11.6 Hz, 1H), 4.47 (dd, J=11.6, 2.6 Hz, 1H), 5.28 (dd, J=2.6, 8.5 Hz, 1H), 6.75 (dd, J=2.6, 8.8 Hz, 1H), 6.88 (d, J=2.6 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 7.21 (d, J=9.1 Hz, 1H), 7.39-7.52 (m, 5H), 8.60 (dd, J=2.8, 9.1 Hz, 1H), 9.05 (d, J=2.8 Hz, 1H).

Workup

  1. additionwas added
  2. filtrationthe precipitated product was filtered
  3. washwashed with water and 2-propanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-61578d7d4782419caed768bd5995343f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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