Potassium Carbonate → 4-chloro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide

HRID 70806Notes

Reaction equation

HRID 70806 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([NH:16][C:17]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N+:25]([O-])=[CH:24][CH:23]=[CH:22]3)=[O:18])=[C:11]([CH3:30])[CH:10]=1)([F:8])[C:4]([F:7])([F:6])[F:5].P(Cl)(Cl)([Cl:35])=O.C(=O)([O-])[O-].[K+].[K+]>>[Cl:35][C:22]1[C:21]2[C:26](=[CH:27][CH:28]=[C:19]([C:17]([NH:16][C:12]3[C:13]([CH3:15])=[CH:14][C:9]([C:3]([F:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:32])([F:31])[F:1])=[CH:10][C:11]=3[CH3:30])=[O:18])[CH:20]=2)[N:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 89106085HCID 89106085, compound

Product 1

HCID 889853914-chloro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamideYield 23%

Conditions

Temperature
100 °C

Procedure

To crude product of N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylpheyl]quinoline-6-carboxamide-1-oxide (97 mg), phosphorus oxychloride (3.0 g) was added and the mixture was stirred under heating at 100° C. for 1 hour. The reaction solution was poured into ice water, neutralized with potassium carbonate and extracted twice with ethyl acetate. The organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain 2-chloro-N-[4-(,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (35 mg, yield 35%) and 4-chloro-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (23 mg, yield 23%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-25f7f8a9b6804759a6f3f8934bfda887
Source dataset
uspto-grants-2014_09
Patent number
US08822691B2

Reaction notes

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