Ammonium Chloride → 2-Chloro-4-methylpyridine-3-carboxamide

HRID 2396583Notes

Reaction equation

HRID 2396583 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:12]1C(C(OCC)=O)=C(C)C=CN=1.[NH4+].[Cl-]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].N>[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([CH3:12])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 825882-ChloronicotinamideHCID 11769512Ethyl 2-chloro-4-methylnicotinate

Product 1

HCID 109428862-Chloro-4-methylpyridine-3-carboxamideYield 64%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 222AmmoniaSolvent

Procedure

In a manner similar to that described for 2-chloro-3-pyridinecarboxamide in Example 13, the title compound (m.p. 168-170) was prepared in 64% yield from 4 g of ethyl 2-chloro-4-methyl-3-pyridinecarboxylate, 1 g of NH4Cl, 30 mL of concentrated aqueous ammonia, and 0.6 of Bu4NBr.

Sources & evidence

ORD record
ord-238cbb26a9994d04abb5a03391bf38d9
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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