Sodium Hydroxide → HCID 19592454, compound

HRID 613476Notes

Reaction equation

HRID 613476 reaction equation
ClC1C=CC=C(Cl)C=1C([O:6][CH2:7][C:8]1[C:17]2[C:12](=[C:13]([NH:18][C:19](=[O:28])[C:20]3[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:27])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)=O.[OH-].[Na+]>C(O)C.O1CCOCC1.ClCCl>[Cl:27][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([Cl:26])[C:20]=1[C:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[CH2:7][OH:6])=[O:28]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 19592453HCID 19592453, compound

Product 1

HCID 19592454HCID 19592454, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(2,6-dichlorobenzoyloxymethyl)-8-(2,6-dichlorobenzoylamino)quinoline (100 mg), 1N sodium hydroxide solution (0.4 ml) in ethanol (2 ml) and dioxane (1 ml) was refluxed for 5 hours. After cooling, the mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate-n-hexane) to give 8-(2,6-dichlorobenzoylamino)-4-hydroxymethylquinoline (20 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-c074ef647109421f93aa68b220ac6177
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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