Benzyl Alcohol → HCID 59710982, compound

HRID 2376798Notes

Reaction equation

HRID 2376798 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26](O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOC(C)=O>[CH2:26]([O:12][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 682631,1'-CarbonyldiimidazoleHCID 825716-Quinolinecarboxylic acid

Product 1

HCID 59710982HCID 59710982, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinoline-6-carboxylic acid (2.0 g, 11.6 mmol) in EtOAc (30 mL) was added carbonyldiimidazole (2.15 g, 13.3 mmol). The resulting mixture was stirred at room temperature for 2 h at which time all solids had dissolved. Benzyl alcohol (1.4 mL) was added and the reaction was stirred overnight. The mixture was then extracted successively with aqueous 1 N HCl (25 mL), aqueous NaHCO3 and brine. Evaporation of the solvent gave a solid, which was triturated with cold 1:1 EtOAc/hexane to afford the title compound as a solid (1.9 g, 62%). 1H NMR (selected signals, CD3OD) δ=9.00 (dd, 1H), 8.61 (d, 1H), 8.34 (d, 1H), 8.29 (dd, 1H), 8.25 (d, 1H), 5.43 (s, 2H)

Workup

  1. dissolutionhad dissolved
  2. stirringthe reaction was stirred overnight
  3. extractionThe mixture was then extracted successively with aqueous 1 N HCl (25 mL), aqueous NaHCO3 and brine
  4. customEvaporation of the solvent
  5. customgave a solid, which
  6. customwas triturated with cold 1:1 EtOAc/hexane

Sources & evidence

ORD record
ord-db4a10e91eab42b7b071e32afe17e4af
Source dataset
uspto-grants-2008_12
Patent number
US07468378B2

Reaction notes

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