2-Chloronicotinic acid → 3-Pyridinecarboxylic acid, 2-phenoxy-

HRID 1731738Notes

Reaction equation

HRID 1731738 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O-:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+]>O>[O:11]([C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 4445035Phenolate Sodium

Product 1

HCID 1234503-Pyridinecarboxylic acid, 2-phenoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The two-step process for producing pure 1-azaxanthone starts from 2-chloronicotinic acid which is reacted with sodium phenoxide at 160°-200° C., the mixture is dissolved in water and acidified, the 2-phenoxynicotinic acid obtained is cyclized with a dehydrating agent, usually polyphosphoric acid, at 120°-200° C. The cooled mixture is dissolved in water and neutralized with an alkaline hydroxide, and the precipitated 1-azaxanthone is washed and recrystallized.

Sources & evidence

ORD record
ord-b51bc0c48c02469aa67669da89d87f93
Source dataset
uspto-grants-1986_11
Patent number
US04623648

Reaction notes

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