Potassium Carbonate → HCID 57861258, compound

HRID 1518056Notes

Reaction equation

HRID 1518056 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH:15]1([CH2:21][NH:22][CH2:23][CH3:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH:15]1([CH2:21][N:22]([C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=3)[N:3]=2)[CH2:23][CH3:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11171028HCID 11171028, compoundHCID 120991792-Chloro-7-fluoroquinoline-3-carbaldehyde

Product 1

HCID 57861258HCID 57861258, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-chloro-7-fluoroquinoline-3-carbaldehyde (200 mg, 0.95 mmol), N-(cyclohexylmethyl)-N-ethylamine (140 mg, 0.99 mmol) and potassium carbonate (140 mg, 1.0 mmol) in toluene (3 mL) is stirred and refluxed for 14 hours. The reaction mixture is cooled to room temperature and then diluted with water and ethyl acetate. The organic layer is washed with 1N HCl, brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give 2-[N-(cyclohexylmethyl)-N-ethylamino]-7-fluoroquinoline-3-carbaldehyde.

Workup

  1. temperaturerefluxed for 14 hours
  2. washThe organic layer is washed with 1N HCl, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f21038f0df14b28bb83e8957eac1bc5
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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