1,1'-Carbonyldiimidazole → HCID 11250167, compound

HRID 327476Notes

Reaction equation

HRID 327476 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[NH:22][CH2:21][CH:20]([N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:19]2>C1COCC1>[CH2:25]([N:24]([CH2:28][CH2:29][CH3:30])[CH:20]1[CH2:19][C:18]2[C:23]3=[C:14]([O:13][C:1](=[O:2])[N:22]3[CH2:21]1)[CH:15]=[CH:16][CH:17]=2)[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 15744975HCID 15744975, compound

Product 1

HCID 11250167HCID 11250167, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (0.46 g, 2.8 mmol) was added to a stirred solution of 1,2,3,4-tetrahydro-8-hydroxy-N,N-dipropyl-3-quinolinamine (0.59 g, 2.4 mmol) in THF (10 mL). After 5 minutes, the solvent was removed and the residue was dissolved in ethyl acetate and chromatographed on silica gel using 5% ethyl acetate in hexane as the initial eluant to give 0.57 g of 5-(dipropylamino)-5,6-dihydro-2H,4H-oxazolo(5,4,3-ij)quinolin-2-one as an oil.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. customchromatographed on silica gel using 5% ethyl acetate in hexane as the initial eluant

Sources & evidence

ORD record
ord-3edb22a2644c4846b9fe5aa0da7cf1bf
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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