4-chloropyridine N-oxide → HCID 58269468, compound

HRID 930647Notes

Reaction equation

HRID 930647 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:15])C2C=CC=CC=2)=[N:6][CH:7]=1.Cl[C:17]1[CH:22]=[CH:21][N+:20]([O-:23])=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:15][C:17]2[CH:22]=[CH:21][N+:20]([O-:23])=[CH:19][CH:18]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 707244-chloropyridine N-oxideHCID 66603325HCID 66603325, compound

Product 1

HCID 58269468HCID 58269468, compoundYield 41%

Procedure

5-Chloro-2-pyridylbenzylalcohol (4.9 g, 34 mmol) and 4-chloropyridine-N-oxide (2.94 g, 22.7 mmol) were reacted according to Example 34 (step a) to provide the title compound (2.2 g, 40%) as a tan solid: 1H NMR (300 MHz, CDCl3) δ 8.58 (d, J=2.2 Hz, 1H), 8.13 (d, J=7.7 Hz, 2H), 7.76-7.72 (dd, J=8.4, 2.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).

Sources & evidence

ORD record
ord-8cc594515db343c3b58034742140888a
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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