Hydrochloric Acid → 5-Chloronicotinic acid

HRID 860495Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[OH-].[Na+].Cl>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 69943215-Chloronicotinate

Product 1

HCID 2479865-Chloronicotinic acidYield 65.3%

Conditions

Temperature: 60 °C

Procedure

To 5-chloronicotinate (10.5 g) was added 1N NaOH (84.9 mL) at ambient temperature. The mixture was heated at 60° C. for 1 hour. The reaction mixture was adjusted to pH 4–5 with HCl. The precipitate was filtered to give 5-chloronicotinic acid (6.9 g) a colorless solid.

Workup

filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-537602e154b04d0cbb337da3de6eb777
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Reaction notes

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