Dichloromethane → 6-Chloronicotinic acid

HRID 637510Notes

Reaction equation

HRID 637510 reaction equation
CC(OC(C)=O)=O.CCN(CC)CC.[N+:15]1([O-])[C:16](=[CH:20][CH:21]=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])C(O)=O.OC1C=CC(C(O)=O)=CN=1.C(Cl)[Cl:39]>>[Cl:39][C:16]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][N:15]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 136435031-Oxo-1lambda~5~-pyridine-2,5-dicarboxylic acidHCID 178418479HCID 178418479, compound

Product 1

HCID 792226-Chloronicotinic acidYield 53.8%

Procedure

This example proceeded as in Example 1, but the reaction was carried out at 0° to 5° C. the bath used had 25.5 g of Ac2O, 20 g of Et3N, 350 g of CH2Cl2 and 18.3 of isocinchomeronic acid-N-oxide. The yield was 53.8 percent of 6-chloronicotinic acid (2-chloro-5-pyridine carboxylic acid), and 39.0 percent of 6-hydroxynicotinic acid (2-hydroxy-5-pyridine-carboxylic acid).

Workup

  1. customwas carried out at 0° to 5° C.

Sources & evidence

ORD record
ord-ea5c558f9afc490ca49205146ded2cd9
Source dataset
uspto-grants-1985_12
Patent number
US04556716

Reaction notes

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