p-Fluoronitrobenzene → HCID 20537894, compound

HRID 1155759Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.ClC1C=CC(C(O)=O)=NC=1.F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[N:6][CH:7]=1

Participants

Reactant 3

HCID 9590p-Fluoronitrobenzene

HCID 27628725-Chloro-2-picolinic acid

HCID 20537893(5-Chloropyridin-2-yl)methanol

Product 1

HCID 20537894HCID 20537894, compound

Procedure

Following the procedure of Example 1, 5-chloro-2-pyridinemethanol, prepared from 5-chloropicolinic acid, is reacted with 1-fluoro-4-nitrobenzene to give 5-chloro-2-(4-nitrophenoxy)methylpyridine, which is converted to 5-chloro-2-(4-aminophenoxy)methylpyridine by reduction with iron and ammonium chloride. The 5-chloro-2-(4-aminophenoxy)methylpyridine and 3,4,5,6-tetrahydrophthalic anhydride are reacted to yield the final product N-4-[2-(5-chloropyridyl)methoxy]phenyl-3,4,5,6-tetrahydrophthalimide.

Sources & evidence

ORD record: ord-c2c67b221dd5435aa8b1871984c00fdc
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04332944

Reaction notes

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