Dichloromethane → 6-Chloronicotinic acid

HRID 637509Notes

Reaction equation

HRID 637509 reaction equation
C(N(CC)CC)C.O[C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1.C(Cl)[Cl:19]>>[Cl:19][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 178418479HCID 178418479, compound

Product 1

HCID 792226-Chloronicotinic acidYield 58.1%

Procedure

This example proceeded as in Example 1, but with use of 500 g of CH2Cl2 and 0.3 mole of triethylamine. The yield of 13.9 g of product mixture (content of nicotinic derivatives was 98.5 percent; the ratio of ClNS/HNS was 64/36) corresponded to a yield of 58.1 percent of 6-chloronicotinic acid and 32.7 percent of 6-hydroxynicotinic acid, related to the amount of isocinchomeronic acid-N-oxide used.

Sources & evidence

ORD record
ord-e698a4f5231f4a37bf071a8d6cce3727
Source dataset
uspto-grants-1985_12
Patent number
US04556716

Reaction notes

Loading…