Potassium Carbonate → HCID 67773395, compound

HRID 2367922Notes

Reaction equation

HRID 2367922 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([OH:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:16]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:16]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:14][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:13]=[CH:12]2)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11550568Tert-butyl 6-bromohexanoateHCID 12336161Methyl 8-Hydroxyquinoline-2-Carboxylate

Product 1

HCID 67773395HCID 67773395, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8-hydroxyquinaldic acid methyl ester (406 mg, 2 mmol, 1 eq.) and t-butyl-6-bromohexanoate (754 mg, 3 mmol, 1.5 eq.) in DMF (5 mL) was added potassium carbonate (828 mg, 6 mmol, 3 eq.). The mixture was stirred vigorously for 3 h at 60° C., and then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo. Crude product was purified by flash chromatography on silica using ethyl acetate:hexanes gradient to provide 617 mg of 1. Yield 86%. MS m/z 374 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with NaH2PO4 buffer (pH 5, 1M) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-086bd1d8b51b4359ab4b6a944e3bdf90
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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