Phosphorus oxychloride → 2,6-Dichloro-N-(2-cyclohexylethyl)-5-quinolinecarboxamide

HRID 2217899Notes

Reaction equation

HRID 2217899 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:8]([C:18]([NH:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:19])=[C:9]2[C:14](=[CH:15][CH:16]=1)[N+:13](O)=[CH:12][CH:11]=[CH:10]2>>[Cl:3][C:12]1[CH:11]=[CH:10][C:9]2[C:8]([C:18]([NH:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:19])=[C:7]([Cl:6])[CH:16]=[CH:15][C:14]=2[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 688102886-Chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-1-hydroxy-quinolinium

Product 1

HCID 860128612,6-Dichloro-N-(2-cyclohexylethyl)-5-quinolinecarboxamide

Conditions

Temperature
60 °C

Procedure

Phosphorous oxychloride (2 mL) was added to 6-chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-1-hydroxy-quinolinium Example 94(c)) (0.089 g) and the mixture heated at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and added to water. The aqueous was extracted with ethyl acetate and the combined organics dried filtered and evaporated give the sub titled compound as a solid (0.079 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionadded to water
  3. extractionThe aqueous was extracted with ethyl acetate
  4. customthe combined organics dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e9590b8ba317452c8281b21c4a6bd34f
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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