6-Chloronicotinic acid → HCID 86613584, compound

HRID 2421211Notes

Reaction equation

HRID 2421211 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=O)=[CH:20][N:19]=1.[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]2[O:14][C:13]([C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:15][N:16]=2)=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 792226-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chloride

Product 1

HCID 86613584HCID 86613584, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (5.00 g, 23.0 mmol) in dichloromethane (100 mL) was added 6-chloronicotinic acid (4.71 g, 29.9 mmol) and 2-chloro-1,3-dimethylimidazolium chloride (8.56 g, 50.6 mmol). After the suspension was stirred for 15 min at ambient temperature, it was cooled to 0° C. and N,N-diisopropyl ethyl amine (19.7 mL, 115 mmol) was added slowly. The reaction mixture was stirred for 18 h while warming to ambient temperature. It was washed with aqueous sodium carbonate (saturated) and the aqueous layers were extracted with dichloromethane. Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 50:50) afforded the title compound (4.78 g, 61%) as a light yellow solid. MS: m/e=339.2 [M+H]+.

Workup

  1. temperatureit was cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 18 h
  3. temperaturewhile warming to ambient temperature
  4. washIt was washed with aqueous sodium carbonate (saturated)
  5. extractionthe aqueous layers were extracted with dichloromethane
  6. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 50:50)

Sources & evidence

ORD record
ord-6f1b8dfef3974043b48019373a3b1bbc
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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