Dichloromethane → 6-Chloronicotinic acid

HRID 637511Notes

Reaction equation

HRID 637511 reaction equation
[N+:1]1([O-])[C:2](=[CH:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])C(O)=O.CC(OC(C)=O)=O.OC1C=CC(C(O)=O)=CN=1.C(Cl)[Cl:32]>CCN(CC)CC>[Cl:32][C:2]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][N:1]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 136435031-Oxo-1lambda~5~-pyridine-2,5-dicarboxylic acidHCID 178418479HCID 178418479, compound

Product 1

HCID 792226-Chloronicotinic acidYield 40.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

A sludge of 50 g of CH2Cl2, 10 g of Et3N and 9.1 g of isocinchomeronic acid-N-oxide was placed in an autoclave. Under 4.5 atu. and at 65° C., a mixture of 10.2 g of Ac2O, 5 g of Et3N and 50 g of CH2Cl2 was additionally pumped in. At the end of the addition, the reaction mixture was processed as in Example 1. The yield was 40.8 percent of 2-chloro-5-pyridine carboxylic acid (6-chloronicotinic acid) and 44.2 percent of 2-hydroxy-5-pyridine carboxylic acid (6-hydroxynicotinic acid).

Workup

  1. additionAt the end of the addition

Sources & evidence

ORD record
ord-492d721a0e764f458c2d4d734facc14e
Source dataset
uspto-grants-1985_12
Patent number
US04556716

Reaction notes

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