1,1'-Carbonyldiimidazole → HCID 53302817, compound

HRID 1025544Notes

Reaction equation

HRID 1025544 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.N1(C(N2C=CN=C2)=O)C=CN=C1.[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][NH:28]1>C1COCC1>[OH:1][C:2]1[C:3]([C:12]([N:28]2[CH2:29][C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:27]2)=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 422478Isoindoline

Product 1

HCID 53302817HCID 53302817, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-hydroxyquinoline-7-carboxylic acid (189 mg, 1.0 mmol) and di(1H-imidazol-1-yl)methanone (162.2 mg, 1.0 mmol) in THF (10 mL) was heated to reflux for 4 h, under nitrogen. The reaction mixture was allowed to cool to RT and isoindoline (95.3 mg, 0.80 mmol) was added. The resulting mixture was stirred at RT for 3 h and then left to stand at RT overnight. The reaction mixture was then quenched with H2O and an aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1) affording the title compound (123 mg, 0.42 mmol) as a light brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h, under nitrogen
  3. waitleft
  4. waitto stand at RT overnight
  5. customThe reaction mixture was then quenched with H2O
  6. extractionan aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM
  7. dry with materialThe separated organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1)

Sources & evidence

ORD record
ord-f47925b3f9064ff9be1e56dc499b5b5f
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Reaction notes

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