Potassium Carbonate → HCID 54085662, compound

HRID 1739666Notes

Reaction equation

HRID 1739666 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].ClC1C(Cl)=N[CH:16]=[C:17]([CH:21]=1)[C:18](O)=O.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=[N:35][O:36][CH3:37])[C:31]([NH:33][CH3:34])=[O:32].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.C(Cl)Cl>[CH3:37][O:36][N:35]=[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O:23][C:3]1[C:2]([Cl:1])=[CH:10][C:6]([C:7]([O:9][C:17]([CH3:21])([CH3:18])[CH3:16])=[O:8])=[CH:5][N:4]=1)[C:31]([NH:33][CH3:34])=[O:32]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2479875,6-Dichloronicotinic acidHCID 36715795-chloro-6-fluoronicotinic acidHCID 136045378N-methyl-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide

Product 1

HCID 54085662HCID 54085662, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flask equipped with magnetic stirrer was added 5,6-dichloronicotinic acid: t-butyl ester (5.0 g, 0.02 mol), n-methylpyrrolidinone (NMP) (5mL), diglyme (1 mL, internal standard) and spray dried KF (5.8 g, 0.1 mol). The slurry was heated to 120° C. for three hours. The mixture was cooled and partitioned between 1,1,2,2-tetrachloroethylene (30 mL) and water. The aqueous phase was extracted with 1,1,2,2,-tetrachloroethylene (30 mL) and the organic phases combined, extracted with 1N NaOH, dried (Na2SO4) and the solvent removed in vacuo to give 3.3 g of solid product that was determined to be 70% 5-chloro-6-fluoronicotinic acid: t-butyl ester and 30% 5,6-dichloronicotinic acid: t-butyl ester. This product was added to a mixture of methylene chloride (10 mL), 2-hydroxy-α-methyoxyimino-N-methyl-benzeneacetamide (0.5 g, 2.4 mmol), powdered potassium carbonate (0.82 g, 6.0 mmol) and tetra-butylammonium bromide (0.08 g, 0.25 mmol). After 24 hours, the mixture was added to ether and extracted with dilute sulfuric acid, water, and 1N NaOH. The solvent was removed in vacuo and the residue was given a chromatographic separation over silica gel using 15% acetonitrile: 85% methylene chloride to give α-(Methoxyimino)-N-methyl-2-[[3-chloro-5-(t-butoxycarbonyl)-2-pyridinyl]oxy]-benzeneacetamide (0.169 g).

Workup

  1. extractionextracted with dilute sulfuric acid, water, and 1N NaOH
  2. customThe solvent was removed in vacuo
  3. customa chromatographic separation over silica gel using 15% acetonitrile

Sources & evidence

ORD record
ord-618b111aa19045af8098819215b411fc
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

Loading…