Thionyl Chloride → 2-Chloro-N-[2-(ethylamino)pyridin-3-yl]-5-nitropyridine-3-carboxamide

HRID 53535Notes

Reaction equation

HRID 53535 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[C:20]([NH:25][CH2:26][CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:1][C:2]1[C:3]([C:4]([NH:18][C:19]2[C:20]([NH:25][CH2:26][CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:6])=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 125426642-Chloro-5-nitropyridine-3-carboxylic acidHCID 13451717N~2~-Ethylpyridine-2,3-diamine

Product 1

HCID 197111082-Chloro-N-[2-(ethylamino)pyridin-3-yl]-5-nitropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.21 g of 2-chloro-5-nitronicotinoyl chloride (obtained by nitrating 2-hydroxynicotinic acid, followed by conversion to 2-chloro-5-nitronicotinic acid, which was then treated with thionyl chloride) in 10 ml of tetrahydrofuran was slowly added over 15 minutes to a cooled, stirred mixture of 1.34 g of 3-Amino-2-ethylaminopyridine, 1.29 g of diisopropylethylamine, and 40 ml of tetrahydrofuran. The resulting mixture was allowed to stir overnight at room temperature, and then concentrated in vacuo. The title compound (2.30 g, m.p. 185°-186° C.), which precipitated out when the residue was treated with methylene chloride, was suitable for use in the next reaction.

Workup

  1. additionwas slowly added over 15 minutes to a cooled
  2. stirringto stir overnight at room temperature
  3. concentrationconcentrated in vacuo
  4. customThe title compound (2.30 g, m.p. 185°-186° C.), which precipitated out when the residue
  5. additionwas treated with methylene chloride
  6. customwas suitable for use in the next reaction

Sources & evidence

ORD record
ord-f2915d0b82a44f5698c0cb41fe540911
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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