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

HRID 31219Notes

Reaction equation

HRID 31219 reaction equation
[C:1]1([CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([O:17]C4C=CC([N+]([O-])=O)=CN=4)=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2OC3C=CC(O)=CC=3OC2)C=CC=CC=1.Cl[C:45]1[C:50]([N+:51]([O-:53])=[O:52])=[CH:49][CH:48]=[CH:47][N:46]=1>>[C:1]1([CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([O:17][C:45]4[C:50]([N+:51]([O-:53])=[O:52])=[CH:49][CH:48]=[CH:47][N:46]=4)=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 179785012-(2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-5-nitropyridineHCID 179785732,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-ol

Product 1

HCID 179785092-(2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-3-nitropyridine

Procedure

2-(2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-3-nitropyridine was prepared in the same way as 2-(2,3-dihydro-2-phenyl-benzo[1,4]dioxin-6-yloxy)-5-nitropyridine above from 2,3-dihydro-2-phenyl-benzo[1,4]dioxin-6-ol (80 mg) and 2-chloro-3-nitropyridine (56 mg). Yield is 30 mg and mp <60° C. 1H NMR (DMSO-d6) δ=4.16 (dd, J=8.6, 11.4 Hz, 1H), 4.46 (dd, J=11.4, 2.5 Hz, 1H), 5.27 (dd, J=2.5, 8.6 Hz, 1H), 6.73 (dd, J=2.5, 8.6 Hz, 1H), 6.85 (d, J=2.5 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 7.34-7.52 (m, 6H), 8.43 (dd, J=1.9, 4.8 Hz, 1H), 8.55 (dd, J=7.8, 1,9 Hz, 1H).

Sources & evidence

ORD record
ord-aa86d10ad7734296b0e0b9d02b736cd5
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…